4-Haloalkyl-3-heterocyclylpyridines and 4-haloalkyl-5-heterocyclyl-pyrimidines, processes for their preparation, compositions comprising them, and their use as pesticides

ABSTRACT

4-Haloalkyl-3-heterocyclylpyridines and 4-haloalkyl-5-heterocyclyl-pyrimidines, processes for their preparation, compositions comprising them, and their use as pesticidesThe present invention relates to 4-haloalkyl-3-heterocyclylpyridines and 4-haloalkyl-5-heterocyclylpyrimidines of the formula (I), to processes for their preparation, to compositions comprising them, and to the use of these compounds for controlling animal pests, in particular insects, spider mites, ectoparasites and helminths.In the formula (I), Q is a 5-membered heterocyclic group which is optionally substituted by halogen or organic radicals, Y is halo-C1-C6-alkyl, X is CH or N and m is 0 or 1.

This application is a divisional of application U.S. Ser. No. 09/096,748, filed on Jun. 12, 1998, now U.S. Pat. No. 6,239,160, which claims priority to German application 197 25 450.0, filed Jun. 16, 1997.

DESCRIPTION

The present invention relates to 4-haloalkyl-3-heterocyclylpyridines and 4-haloalkyl-5-heterocyclylpyrimidines, to processes for their preparation, to compositions comprising them and to the use of novel and known 4-haloalkyl-3-heterocyclylpyridines and 4-haloalkyl-5-heterocyclylpyrimidines for controlling animal pests, in particular insects, spider mites, ectoparasites and helminths.

It is already known that appropriately substituted pyridines or pyrimidines have acaricidal and insecticidal activity. Thus, WO 95/07891 describes pyridines which carry a cycloalkyl radical in position 4 which is linked via a hetero atom and a group of various substituents in position 3. WO 93119050 discloses 4-cycloalkylamino-and 4-cycloalkoxypyrimidines which carry in position 5 inter alia alkyl, alkoxy or haloalkoxy groups. However, the desired activity against the harmful organisms is not always sufficient. Additionally, these compounds often have undesirable toxicologic properties toward mammals and aquatic living beings.

Pyridyl-1,2,4-thiadiazoles having fungicidal properties are described in DE-A 42 39 727. The compounds disclosed therein carry the thiadiazole ring in position 2, 3 or 4 of the unsubstituted pyridine.

EP-A 0 371 925 discloses some 1,3,4-oxadiazolyl- and 1,3,4-thiadiazolyl-pyrimidines having nematicidal and fungicidal properties. In the biologically effective compounds disclosed in this publication, the pyrimidine carries the oxadiazolyl or thiadiazolyl ring either

a) in position 5 and is optionally substituted by a thiomethyl group in position 2, or

b) in position 2 and is optionally substituted in position 4 and 6, in each case by a methyl group.

Aryltriazole derivatives for use as pesticides are known from EP-A 0,185,256. In addition to the phenyltriazoles, which are particularly preferred, three haloalkyl-3-pyridyltriazoles are disclosed:

3-(2-chlorophenyl)-1-methyl-5-(4-trifluoromethyl-3-pyridyl)-1H-1,2,4-triazole

3-(2,6-difluorophenyl)-1-methyl-5-(4-trifluoromethyl-3-pyridyl)-1H-1,2,4-triazole and

3-(2-chloro4-fluorophenyl)-1-methyl-5-(4-trifluoromethyl-3-pyridyl)-1H-1,2,4-triazole,

their desired activity at low application rates, however, is not always satisfactory, especially when controlling insects and spider mites.

Some commercially available 4-haloalkyl-3-heterocyclylpyridines are known from the Maybridge Catalogue 1996/1997, Maybridge Chemical CO. LTD., Trevillett Tintagel, GB:

3-(3,5-dichlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(4-trifluoromethyl-3-pyridyl)-3-phenyl-1,2,4-oxadiazole

3-(4-trifluoromethyl-3-pyridyl)-5-phenyl-1,2,4-oxadiazole

5-(2-chlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(3-chlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(4-chlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4oxadiazole

5-(2-fluorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(4-fluorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(2,4-dichlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(3,4-dichlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(3,5-dichlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(2,6-dichloro-4-pyridyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

5-(3,5-bistrifluoromethylphenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

2-(2-chlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole

2-(3-chlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole

2-(4-chlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole

2-(2-trifluoromethoxyphenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole

2-(4-trifluoromethoxyphenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole

2-(4-trifluoromethyl-3-pyridyl)-5-phenyl-1,3,4-oxadiazole

2-(4-trifluoromethyl-3-pyridyl)-4-methylthiazolecarbohydrazide

ethyl 2-(4-trifluoromethyl-3-pyridyl)-4-methylthiazolecarboxylate

N-(4-chlorophenyl)carbonyl-N′-[2-(4-trifluoromethyl-3-pyridyl)4-methyl-5-thiazolyl]carbonylhydrazine

2-(4-trifluoromethyl-3-pyridyl)-4-thiazolecarbohydrazide

4-(4-chlorophenyl)-2-(4-trifluoromethyl-3-pyridyl)thiazole

4-(4-cyanophenyl)-2-(4-trifluoromethyl-3-py(idyl)thiazole

N-(4-trifluoromethylphenyl)carbonyl-N′-[2-(4-trifluoromethyl-3-pyridyl)-4-thiazolyl]carbonylhydrazine

2-(2-(4-trifluoromethyl-3-pyridyl)thiazolyl)-5-chloro-3-methylbenzo[b]thiophene

2-(4-chlorophenylmethylthio)-5-(4-trifluoromethyl-3-pyridyl)-1 -methyl-1 H-1,3,4-triazole

2-(4-chlorophenylcarbonylmethylthio)-5-(4-trifluoromethyl-3-pyridyl)-1-methyl-1H-1,3,4-triazole and

2-ethoxycarbonylmethylthio-5-(4-trifluoromethyl-3-pyridyl)-1-methyl-1H-1,3,4-triazole.

However, a biological activity toward harmful organisms has hitherto not been disclosed.

It is an object of the present invention to provide compounds having good insecticidal and acaricidal properties and simultaneously low toxicity toward mammals and aquatic living beings.

It has now been found that compounds of the formula I, optionally as salts, have a wider activity spectrum against animal pests and simultaneously more favorable toxicologic properties toward mammals and aquatic living beings than the prior art compounds.

In the formula (I):

Y is halo-C₁-C₆-alkyl;

x is CH or N;

m is 0 or 1;

Q is a 5-membered heterocyclic group

in which

a) X¹ = W, X² = NR^(a), X³ = CR^(b)R¹ or b) X¹ = NR^(a), X² = CR^(b)R¹, X³ = W or c) X¹ = V, X² = CR^(a)R¹, X³ = NR^(b) or d) X¹ = V, X² = CR^(a)R², X³ = CR^(b)R³ or e) X¹ = V, X² = CR⁴R⁵, X³ = CR⁶R⁷ or f) X¹ = NR^(a), X² = CR^(b)R¹, X³ = NR⁸;

R^(a) and R^(b) together are a bond

V is oxygen, sulfur or NR⁹;

W is oxygen or sulfur;

R¹ is hydrogen,

(C₁-C₂₀)-alkyl, (C₂-C₂₀)-alkenyl, (C₂-C₂₀)-alkynyl, (C₃-C₈)-cycloalkyl,

(C₄-C₈)-cycloalkenyl, (C₆-C₈)-cycloalkynyl,

where the six last-mentioned radicals are optionally substituted by one or more radicals from the group

halogen, cyano, nitro, hydroxyl, —C(═W)R¹⁰, —C(═NOR¹⁰)R¹⁰, —(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OC(═W)OR¹⁰, —NR¹⁰C(═W)R¹⁰, —N[C(═W)R¹⁰]₂, —NR¹⁰C(═W)OR¹⁰, —C(═W)NR¹⁰—NR¹⁰C(═W)NR¹⁰—NR¹⁰[C(═W)R¹⁰], —NR¹⁰—C(═W)NR¹⁰ ₂, —NR¹⁰—NR¹⁰C(═W)R¹⁰, —NR¹⁰—N[C(═W)R¹⁰]₂, —N[(C═W)R¹⁰]—NR¹⁰ ₂, —NR¹⁰—NR¹⁰[(C═W)R¹⁰], —NR¹⁰—NR¹⁰[(C═W)WR¹⁰], —NR¹⁰—R¹⁰[(C═W)NR¹⁰ ₂], —NR¹⁰(C═NR¹⁰)R¹⁰, —NR¹⁰(C═NR¹⁰)NR¹⁰ ₂, —O—NR¹⁰ ₂, —O—NR¹⁰(C═W)R¹⁰, —SO₂NR¹⁰ ₂, —NR¹⁰SO₂R¹⁰, —SO₂OR¹⁰, —OSO₂R¹⁰—OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SiR¹⁰ ₃, —SeR¹⁰, —PR¹⁰ ₂, —P(═W)R¹⁰ ₂, —SOR¹⁰, —SO₂R¹⁰, —PW₂R¹⁰ ₂, —PW₃R¹⁰ ₂, aryl and heterocyclyl, the two last-mentioned radicals optionally being substituted by one or more radicals from the group

(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₆-C₈)-cycloalkynyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl, halogen, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SiR¹⁰ ₃, —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —SOR¹⁰, —SO₂R¹⁰, nitro, cyano and hydroxyl, aryl,

which is optionally substituted by one or more radicals from the group (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl and (C₆-C₈)-cycloalkynyl,

where these six abovementioned radicals are optionally substituted by one or more radicals from the group

halogen, cyano, nitro, —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰ and —SO₂R¹⁰,

halogen, cyano, nitro, —(═W)R¹⁰, —C(═NOR¹⁰)R¹⁰, —C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OC(═W)OR¹⁰, —NR¹⁰C(═W)R¹⁰, —N[C(═W)R¹⁰]₂, —NR¹⁰C(═W)OR¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SiR¹⁰ ₃, —PR¹⁰ ₂, —SOR¹⁰, —SO₂R¹⁰, —PW₂R¹⁰ ₂ and —PW₃R¹⁰ ₂, heterocyclyl,

which is optionally substituted by one or more radicals from the group (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl and (C₆-C₈)-cycloalkynyl,

where the six abovementioned radicals are optionally substituted by one or more radicals from the group

cyano, nitro, halogen, —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —NR¹⁰C(═W)R¹⁰, —N[C(═W)R¹⁰]₂, —OC(═W)R¹⁰, —OC(═W)OR¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰ and —SO₂R¹⁰);

halogen, cyano, nitro, —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰ and —SO₂R¹⁰; —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰, —SO₂R¹⁰, —C(═W)R¹⁰, —C(═NOR¹⁰)R¹⁰, —C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OC(═W)OR¹⁰, —NR¹⁰C(═W)R¹⁰, —N[C(═W)R¹⁰]₂, —NR¹⁰C(═W)OR¹⁰, —C(═W)NR¹⁰—NR¹⁰ ₂, —C(═W)NR¹⁰—NR¹⁰[C(═W)R¹⁰], —NR¹⁰—C(═W)NR¹⁰ ₂, —NR¹⁰—NR¹⁰C(═W)R¹⁰, —NR¹⁰—NC(═W)R¹⁰ ₂, —N(C═W)R¹⁰—NR¹⁰ ₂, —NR¹⁰—NR¹⁰[(C═W)R¹⁰], —NR¹⁰—NR¹⁰[(C═W)WR¹⁰], —NR¹⁰—NR¹⁰[(C═W)NR¹⁰ ₂], —NR¹⁰(C═NR¹⁰)R¹⁰, —NR¹⁰(C═NR¹⁰)NR¹⁰ ₂, —O—NR¹⁰ ₂, —O—NR¹⁰(C═W)R¹⁰, —SO₂NR¹⁰ ₂, —NR¹⁰SO₂R¹⁰, —SO₂OR¹⁰, —OSO₂R¹⁰, —SC(═W)R¹⁰, —SC(═W)OR¹⁰, —SC(═W)R¹⁰, —PR¹⁰ ₂, —PW₂R¹⁰ ₂, —PW₃R¹⁰ ₂, SiR¹⁰ ₃ or halogen;

R² and R³ independently of one another have the definitions given in R¹;

R² and R³ together form a 5- to 7-membered ring which may be partially or fully unsaturated and may be interrupted by one or more atoms from the group nitrogen, oxygen and sulfur, the oxygen atoms not being directly adjacent to one another, and the ring optionally being substituted by one or more, but at most 5, radicals R¹; R⁴ and R⁶ independently of one another have the definitions given in R¹;

R⁴ and R⁶ together form a 4- to 7-membered ring which may be partially or fully unsaturated and may be interrupted by one or more atoms from the group nitrogen, oxygen and sulfur, the oxygen atoms not being directly adjacent to one another, and the ring optionally being substituted by one or more, but at most 5, radicals R¹;

R⁵ and R⁷ independently of one another are hydrogen,

(C₁-C₂₀)-alkyl, (C₂-C₂₀)-alkenyl, (C₂-C₂₀)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₆-C₈)-cycloalkynyl,

where the six last-mentioned radicals are optionally substituted by one or more radicals from the group

halogen, cyano, nitro, hydroxyl, —C(═W)R¹⁰, —C(═NOR¹⁰)R¹⁰, —C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OC(═W)OR¹⁰, —NR¹⁰C(═W)R¹⁰, —N[C(═W)R¹⁰]₂, —NR¹⁰C(═W)OR¹⁰, —C(═W)NR¹⁰—NR¹⁰ ₂, —(═W)NR¹⁰—NR¹⁰[C(═W)R¹⁰], —NR¹⁰—C(═W)NR¹⁰ ₂, —NR¹⁰—NR¹⁰C(═W)R¹⁰, —NR¹⁰—N[C(═W)R¹⁰]₂, —N[(C═W)R¹⁰]—NR¹⁰ ₂, —NR¹⁰—NR¹⁰[(C═W)R¹⁰], —NR¹⁰—NR¹⁰[(C═W)WR¹⁰], —NR¹⁰—NR¹⁰[(C═W)NR¹⁰ ₂], —NR¹⁰(C═NR¹⁰)R¹⁰, —NR¹⁰(C═NR¹⁰)NR¹⁰ ₂, —O—NR¹⁰ ₂, —O—NR¹⁰(C═W)R¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SiR¹⁰ ₃, —SeR¹⁰, —PR¹⁰ ₂, —P(═W)R¹⁰ ₂, —SOR¹⁰, —SO₂R¹⁰, —PW₂R¹⁰ ₂, —PW₃R¹⁰ ₂, aryl and heterocyclyl, of which the two mentioned last are optionally substituted by one or more radicals from the group

(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₆-C₈)-cycloalkynyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl, halogen, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SiR¹⁰ ₃, —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —SOR¹⁰, —SO₂R¹⁰, nitro, cyano and hydroxyl, aryl,

which is optionally substituted by one or more radicals from the group (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl and (C₆-C₈)-cycloalkynyl,

where these six abovementioned radicals are optionally substituted by one or more radicals from the group

halogen, cyano, nitro, —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰ and —SO₂R¹⁰;

halogen, cyano, nitro, —C(═W)R¹⁰, —C(═NOR¹⁰)R¹⁰, —C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OC(═W)OR¹⁰, —NR¹⁰C(═W)R¹⁰, —N[C(═W)R¹⁰]₂, —NR¹⁰C(═W)OR₁₀, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SiR¹⁰ ₃, —PR¹⁰ ₂, —SOR¹⁰, —SO₂R¹⁰, —PW₂R¹⁰ ₂ and —PW₃R¹⁰ ₂; pyridyl,

which is optionally substituted by one or more radicals from the group (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl and (C₆-C₈)-cycloalkynyl,

where the six abovementioned radicals are optionally substituted by one or more radicals from the group

cyano, nitro, halogen, —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰ and —SO₂R¹⁰,

halogen, cyano, nitro, —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰ and —S¹⁰ ₂R¹⁰;

—C(═W)R¹⁰, —C(═NOR¹⁰)R¹⁰, —C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂ or halogen;

R⁴ and R⁵ together form a 4- to 7-membered ring which may be partially unsaturated and may be interrupted by one or more atoms from the group nitrogen, oxygen and sulfur, oxygen atoms not being directly adjacent to one another, and the ring optionally being substituted by one or more, but at most 5, radicals R¹; R⁴ and R⁵ together form one of the groups ═O, ═S or ═N—R⁹; R⁶ and R⁷ together form a 5- to 7-membered ring which may be partially unsaturated and may be interrupted by one or more atoms from the group nitrogen, oxygen and sulfur, oxygen atoms not being directly adjacent to one another, and the ring optionally being substituted by one or more, but at most 5, radicals R¹;

R⁶ and R⁷ together form one of the groups ═O, ═S or ═N—R⁹;

R⁸ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenyl, (C₄-C₆)-cycloalkenyl-(C₁-C₄)-alkenyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl-C₄-C₈)-cycloalkenyl, (C₂-C₆)-alkenyl-C₄-C₈)-cycloalkenyl,

where the fourteen last-mentioned radicals are optionally substituted by one or more radicals from the group

halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkyloxy, (C₂-C₆)-haloalkenyloxy, (C₂-C₆)-haloalkynyloxy, (C₃-C₈)-cycloalkoxy, (C₄-C₈)-cycloalkenyloxy, (C₃-C₈)-halocycloalkoxy, (C₄-C₈)-halocycloalkenyloxy, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkoxy, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkoxy, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenyloxy, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyloxy, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkoxy, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkoxy, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkoxy, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenyloxy, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenyloxy, (C₁-C₄)-alkoxy-(C₁-C₆)-alkoxy, (C₁-C₄)-alkoxy-(C₂-C₆)-alkenyloxy, carbamoyl, (C₁-C₆)-mono- or dialkylcarbamoyl, (C₁-C₆)-mono- or dihaloalkylcarbamoyl, (C₃-C₈)-mono- or dicycloalkylcarbamoyl, (C₁-C₆)-alkoxycarbonyl, (C₃-C₈)-cycloalkoxycarbonyl, (C₁-C₆)-alkanoyloxy, (C₃-C₈)-cycloalkanoyloxy, (C₁-C₆)-haloalkoxycarbonyl, (C₁-C₆)-haloalkanoyloxy, (C₁-C₆)-alkaneamido, (C₁-C₆)-haloalkaneamido, (C₂-C₆)-alkeneamido, (C₃-C₈)-cycloalkaneamido, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkaneamido, (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio, (C₁-C₆)-haloalkylthio, (C₂-C₆)-haloalkenylthio, (C₂-C₆)-haloalkynylthio, (C₃-C₈)-cycloalkylthio, (C₄-C₈)-cycloalkenylthio, (C₃-C₈)-halocycloalkylthio, (C₄-C₈)-halocycloalkenylthio, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylthio, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylthio, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylthio, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylthio, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylthio, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylthio, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylthio, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylthio, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylthio, (C₁-C₆)-alkylsulfinyl, (C₂-C₆)-alkenylsulfinyl, (C₂-C₆)-alkynylsulfinyl, (C₁-C₆)-haloalkylsulfinyl, (C₂-C₆)-haloalkenylsulfinyl, (C₂-C₆)-haloalkyny, sulfnyl, (C₃-C₈)-cycloalkylsulinyl, (C₄-C₈)-cycloalkenylsulfinyl, (C₃-C₈)-halocycloalksulfinyl, (C₄-C₈)-halocycloalkenylsulfinyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylsulfinyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylsulfinyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylsulfinyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylsulfinyl, (C₁-C₆)-alkyl-(C₃-C₈)- cycoalkylsulfinyl, (C₂-C₆)- alkenyl-(C₃-C₈)-cycloalkylsulfinyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylsulfinyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylsulfinyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₂-C₆)-alkenylsulfonyl, (C₂-C₆)-alkynylsulfonyl, (C₁-C₆)-haloalkylsulfonyl , (C₂-C₆)-haloalkenylsulfonyl, (C₂-C₆)-haloalkynylsulfonyl, (C₃-C₈)-cycloalkylsulfonyl, (C₄-C₈)-cycloalkenylsulfonyl, (C₃-C₈)-halocycloalkylsulfonyl, (C₄-C₈)-halocycloalkenyisulfonyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylsulfonyl, (C₄-C₈ )-cycloalkenylony-(C₁-C₄)-alkylsulfonyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylsulfonyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylsulfonyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylsulfonyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylsulfonyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylsulfonyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylsulfonyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylsulfonyl, (C₁-C₆)-alkylamino, (C₂-C₆)-alkenylamino, (C₂-C₆)-alkynylamino, (C₁-C₆)-haloalkylamino, (C₂-C₆)-haloalkenylamino, (C₂-C₆)-haloalkynylamino, (C₃-C₈)-cycloalkylamino, (C₄-C₈)-cycloalkenylamino, (C₃-C₈)-halocycloalkamino, (C₄-C₈)-halocycloalkenylamino, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylamino, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylamino, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylamino, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylamino, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylamino, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylamino, (C₂₋C₆)-alkynyl-(C₃-C₈)-cycloalkylamino, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylamino, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylamino, (C₁-C₆)-trialkylsilyl, aryl, aryloxy, arylthio, arylamino, arylcarbamoyl, aroyl, aroyloxy, aryloxycarbonyl, aryl-(C₁-C₄)-alkoxy, aryl-(C₂-C₄)-alkenyloxy, aryl-(C₁-C₄)-alkylthio, aryl-(C₂-C₄)-alkenylthio, aryl-(C₁-C₄)-alkylamino, aryl-(C₂-C₄)-alkenylamino, aryl-(C₁-C₆)-dialkylsilyl, diaryl-(C₁-C₆)-alkylsilyl, triarylsilyl and 5- or 6-membered heterocyclyl, of which the nineteen last-mentioned radicals are optionally substituted in their cyclic moiety by one or more substituents from the group halogen, cyano, nitro, amino, hydroxyl, thio, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-haloalkylthio, (C₁-C₄)-alkylamino, (C₁-C₄)-haloalkylamino, formyl and (C₁-C₄)-alkanoyl; aryl, which is optionally substituted by one or more radicals from the group halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkyloxy, (C₂-C₆)-haloalkenyloxy, (C₂-C₆)-haloalkynyloxy, (C₃-C₈)-cycloalkoxy, (C₄-C₈)-cycloalkenyloxy, (C₃-C₈)-halocycloalkoxy, (C₄-C₈)-halocycloalkenyloxy, carbamoyl, (C₁-C₆)-mono- or dialkylcarbamoyl, (C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-alkanoyloxy, (C₁-C₆)-mono- or dihaloalkylcarbamoyl, (C₁-C₆)-haloalkoxycarbonyl, (C₁-C₆)-haloalkanoyloxy, (C₁-C₆)-alkaneamido, (C₁-C₆)-haloalkaneamido, (C₂-C₆)-alkeneamido, (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio, (C₁-C₆)-haloalkylthio, (C₂-C₆)-haloalkenylthio, (C₂-C₆)-haloalkynylthio, (C₃-C₈)-cycloalkylthio, (C₄-C₈)-cycloalkenylthio, (C₃-C₈)-halocycloalkthio, (C₃-C₈)-halocycloalkenylthio, (C₁-C₆)-alkylsulfinyl, (C₂-C₆)-alkenylsulfinyl, (C₂-C₆)-alkynylsulfinyl, (C₂-C₆)-haloalkylsulfinyl, (C₂-C₆)-haloalkenylsulfinyl, (C₂-C₆)-haloalkynylsulfinyl, (C₃-C₈)-cycloalkylsulfinyl, (C₄-C₈)-cycloalkenylsulfinyl, (C₃-C₈)-halocycloalksulfinyl, (C₄-C₈)-halocycloalkenylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₂-C₆)-alkenylsulfonyl, (C₂-C₆)-alkynylsulfonyl, (C₁-C₆)-haloalkylsulfonyl, (C₂-C₆)-haloalkenylsulfonyl, (C₂-C₆)-haloalkynylsulfonyl, (C₃-C₈)-cycloalkylsulfonyl, (C₄-C₈)-cycloalkenylsulfonyl, (C₃-C₈)-halocycloalksulfonyl, (C₄-C₈)-halocycloalkenylsulfonyl, (C₂-C₆)-alkylamino, (C₂-C₆)-alkenylamino, (C₂-C₆)-alkynylamino, (C₁-C₆)-haloalkylamino, (C₂-C₆)-haloalkenylamino, (C₂-C₆ )-haloalkynylamino, (C₃-C₈)-cycloalkylamino, (C₄-C₈)-cycloalkenylamino, (C₃-C₈)-halocycloalkamino and (C₄-C₈)-halocycloalkenylamino, —C(═W)R¹¹, OR¹¹ or NR¹¹ ₂;

R⁹ is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyl, where the nine last-mentioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆) alkynyloxy and (C₁-C₆)-haloalkyloxy;

R¹⁰ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenyl, where the fourteen last-mentioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkyloxy, (C₂-C₆)-haloalkenyloxy, (C₂-C₆)-haloalkynyloxy, (C₃-C₈)-cycloalkoxy, (C₄-C₈)-cycloalkenyloxy, (C₃-C₈)-halocycloalkoxy, (C₄-C₈)-halocycloalkenyloxy, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkoxy, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkoxy, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenyloxy, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyloxy, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkoxy, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkoxy, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkoxy, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenyloxy, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenyloxy, (C₁-C₄)-alkoxy-(C₁-C₆)-alkoxy, (C₁-C₄)-alkoxy-(C₂-C₆)-alkenyloxy, carbamoyl, (C₁-C₆)-mono- or dialkylcarbamoyl, (C₁-C₆)-mono- or dihaloalkylcarbamoyl, (C₃-C₈)-mono- or dicycloalkylcarbamoyl, (C₁-C₆)-alkoxycarbonyl, (C₃-C₈)-cycloalkoxycarbonyl, (C₁-C₆)-alkanoyloxy, (C₃-C₈)-cycloalkanoyloxy, (C₁-C₆)-haloalkoxycarbonyl, (C₁-C₆)-haloalkanoyloxy, (C₁-C₆)-alkaneamido, (C₁-C₆)-haloalkaneamido, (C₂-C₆)-alkeneamido, (C₃-C₈)-cycloalkaneamido, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkaneamido, (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio, (C₁-C₆)-haloalkylthio, (C₂-C₆)-haloalkenylthio, (C₂-C₆)-haloalkynylthio, (C₃-C₈)-cycloalkylthio, (C₄-C₈)-cycloalkenylthio, (C₃-C₈)-halocycloalkthio, (C₄-C₈)-halocycloalkenylthio, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylthio, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylthio, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylthio, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylthio, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylthio, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylthio, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylthio, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylthio, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylthio, (C₁-C₆)-alkylsulfinyl, (C₂-C₆)-alkenylsulfinyl, (C₂-C₆)-alkynylsulfinyl, (C₁-C₆)-haloalkylsulfinyl, (C₂-C₆)-haloalkenylsulfinyl, (C₂-C₆)-haloalkynylsulfinyl, (C₃-C₈)-cycloalkylsulfinyl, (C₄-C₈)-cycloalkenylsulfinyl, (C₃-C₈)-halocycloalksulfinyl, (C₄-C₈)-halocycloalkenylsulfinyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylsulfinyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylsulfinyl, (C₃-C₈)-cycoalkyl-(C₂-C₄)-alkenylsulfinyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylsulfinyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylsulfinyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylsulfinyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylsulfinyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylsulfinyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₂-C₆)-alkenylsulfonyl, (C₂-C₆)-alkynylsulfonyl, (C₁-C₆)-haloalkylsulfonyl, (C₂-C₆)-haloalkenylsulfonyl, (C₂-C₆)-haloalkynylsulfonyl, (C₃-C₈)-cycloalkylsulfonyl, (C₄-C₈)-cycloalkenylsulfonyl, (C₃-C₈)-halocycloalksulfonyl, (C₄-C₈)-halocycloalkenylsulfonyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylsulfonyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylsulfonyl, (C₃-C₈)- ycloalkyl-(C₂-C₄)-alkenylsulfonyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyl sulfonyl, (C₁-C₈)-alkyl-(C₃-C₈)-cycloalkylsulfonyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylsulfonyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylsulfonyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylsulfonyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylsulfonyl, (C₁-C₆)-alkylamino, (C₂-C₆)-alkenylamino, (C₂-C₆ )-alkyenyl amino, (C₁-C₆)-haloalkylamino, (C₂-C₆)-haloalkenylamino, (C₂-C₆)-haloalkynylamino, (C₃-C₈)-cycloalkylamino, (C₄-C₈)-cycloalkenylamino, (C₃-C₈)-halocycloalkamino, (C₄-C₈)-halocycloalkenylamino, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylamino, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylamino, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylamino, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylamino, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylamino, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylamino, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylamino, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylamino, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylamino, (C₁-C₆)-trialkylsilyl, aryl, aryloxy, arylthio, arylamino, aryl-C₁-C₄)-alkoxy, aryl-(C₂-C₄)-alkenyloxy, aryl-(C₁-C₄)-alkylthio, aryl-(C₂-C₄)-alkenylthio, aryl-(C₁-C₄)-alkylamino, aryl-(C₂-C₄)-alkenylamino, aryl-(C₁-C₆)-dialkylsilyl, diaryl-(C₁-C₆)-alkylsilyl, triarylsilyl and 5- or 6-membered heterocyclyl, where the cyclic moiety of the fourteen last-mentioned radicals is optionally substituted by one or more radicals from the group halogen, cyano, nitro, amino, hydroxyl, thio, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₃-C₈)-cycloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-haloalkylthio, (C₁-C₄)-alkylamino, (C₁-C₄)-haloalkylamino, formyl and (C₁-C₄)-alkanoyl;

aryl, 5- or 6-membered heteroaromatic, where the two last-mentioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkyloxy, (C₂-C₆)-haloalkenyloxy, (C₂-C₆)-haloalkynyloxy, (C₃-C₈)-cycloalkoxy, (C₄-C₈)-cycloalkenyloxy, (C₃-C₈)-halocycloalkoxy, (C₄-C₈)-halocycloalkenyloxy, carbamoyl, (C₁-C₆)-mono- or dialkylcarbamoyl, (C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-alkanoyloxy, (C₁-C₆)-mono- or dihaloalkylcarbamoyl, (C₁-C₆)-haloalkoxycarbonyl, (C₁-C₆)-haloalkanoyloxy, (C₁-C₆)-alkaneamido, (C₁-C₆)-haloalkaneamido, (C₂-C₆)-alkeneamido, (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio, (C₁-C₆)-haloalkylthio, (C₂-C₆)-haloalkenylthio, (C₂-C₆)-haloalkynylthio, (C₃-C₈)-cycloalkylthio, (C₄-C₈)-cycloalkenylthio, (C₃-C₈)-halocycloalkthio, (C₄-C₈)-halocycloalkenylthio, (C₁-C₆)-alkylsulfinyl, (C₂-C₆)-alkenylsulfinyl, (C₂-C₆)-alkynylsulfinyl, (C₁-C₆)-haloalkylsulfinyl, (C₂-C₆)-haloalkenylsulfinyl, (C₂-C₆)-haloalkynylsulfinyl, (C₃-C₈)-cycloalkylsulfinyl, (C₄-C₈)-cycloalkenylsulfinyl, (C₃-C₈)-halocycloalksulfinyl, (C₄-C₈)-halocycloalkenylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₂-C₆)-alkenylsulfonyl, (C₂-C₆)-alkynylsulfonyl, (C₁-C₆)-haloalkylsulfonyl, (C₂-C₆)-haloalkenylsulfonyl, (C₂-C₆)-haloalkynylsulfonyl, (C₃-C₈)-cycloalkylsulfonyl, (C₄-C₈)-cycloalkenylsulfonyl, (C₃-C₈)-halocycloalksulfonyl, (C₄-C₈)-halocycloalkenylsulfonyl, (C₁-C₆)-alkylamino, (C₂-C₆)-alkenylamino, (C₂-C₆)-alkynylamino, (C₁-C₆)-haloalkylamino, (C₂-C₆)-haloalkenylamino, (C₂-C₆)-haloalkynylamino, (C₃-C₈)-cycloalkylamino, (C₄-C₈)cycloalkenylamino, (C₃-C₈)-halocycloalkylamino and (C₄-C₈)-halocycloalkenylamino;

R¹¹ is (C₁-C₁₀)-alkyl, haloalkyl, aryl, which is optionally substituted by one or more radicals from the group halogen, cyano, nitro, (C₁-C₄)-alkoxy, (C₁-C₄)-alkyl, amino, (C₁-C₄)-monoalkylamino and (C₁-C₄)-dialkylamino; NR¹⁰ ₂, OR¹⁰ or SR¹⁰.

The term “halogen” includes fluorine, chlorine, bromine and iodine.

The term “(C₁-C₄)-alkyl” is to be understood as a straight-chain or branched hydrocarbon radical having 1, 2, 3 or 4 carbon atoms, such as, for example, the methyl, ethyl, propyl, isopropyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl radical. Correspondingly, alkyl radicals having a greater range of carbon atoms are to be understood as straight-chain or branched saturated hydrocarbon radicals which contain a number of carbon atoms which corresponds to the range stated. Thus, the term “(C₁-C₆)-alkyl” includes the abovementioned alkyl radicals, and, for example, the pentyl, 2-methylbutyl, 1,1-dimethylpropyl, hexyl radical. The term “(C₁-C₁₀)-alkyl” is to be understood as the abovementioned alkyl radicals, and, for example, the nonyl, 1-decyl or 2-decyl radical and the term “(C₁-C₂₀)-alkyl” is to be understood as the abovementioned alkyl radicals, and, for example, the undecyl, dodecyl, pentadecyl or eicosyl radical.

“(C₁-C₄)-Haloalkyl” is to be understood as an alkyl group mentioned under the term “(C₁-C₄)-alkyl” in which one or more hydrogen atoms are replaced by the same number of identical or different halogen atoms, preferably by fluorine or chlorine, such as the trifluoromethyl, the 1-fluoroethyl, the 2,2,2-trifluoroethyl, the chloromethyl, fluoromethyl, the difluoromethyl and the 1,1,2,2-tetrafluoroethyl group.

“(C₁-C₄)-Alkoxy” is to be understood as an alkoxy group whose hydrocarbon radical has the meaning given under the term “(C₁-C₄)-alkyl”. Alkoxy groups embracing a greater range of carbon atoms are to be understood correspondingly.

The terms “alkenyl” and “alkynyl” having a prefix stating the range of carbon atoms denote a straight-chain or branched hydrocarbon radical having a number of carbon atoms corresponding to the range stated which comprises at least one multiple bond which may be in any position of the unsaturated radical in question. “(C₂-C₄)-Alkenyl” is thus, for example, the vinyl, allyl, 2-methyl-2-propene or 2-butenyl group; “(C₂-C₆)-alkenyl” denotes the abovementioned radicals and, for example, the pentenyl, 2-methylpentenyl or the hexenyl group. The term “(C₂-C₂₀)-alkenyl” is to be understood as the abovementioned radicals and, for example, the 2-decenyl or the 2-eicosenyl group. “(C₂-C₄)-Alkynyl” is, for example, the ethynyl, propargyl, 2-methyl-2-propyne or 2-butynyl group. “(C₂-C₆)-Alkynyl” is to be understood as the abovementioned radicals and, for example, the 2-pentynyl- or the 2-hexynyl group and “(C₂-C₂₀)-alkynyl” is to be understood as the abovementioned radicals and, for example, the 2-octynyl or the 2-decynyl group.

“(C₃-C₈)-cycloalkyl” denotes monocyclic alkyl radicals, such as the cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl radical and bicyclic alkyl radicals, such as the norbornyl radical.

The term “(C₃-C₈)-cycloalkyl-(C₁-C₄)-alkyl” is to be understood as, for example, the cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylbutyl radical, and the term “(C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl is to be understood as, for example, the 1-methylcyclopropyl, 1-methylcyclopentyl, 1-methylcyclohexyl, 3-hexylcyclobutyl and 4-tert-butyl-cyclohexyl radical.

“(C₁-C₄)-Alkoxy-(C₁-C₆)-alkyloxy” is an alkoxy group as defined above which is substituted by a further alkoxy group, such as, for example, 1-ethoxyethoxy.

“(C₃-C₈)-cycloalkoxy” or “(C₃-C₈)-cycloalkylthio” is to be understood as one of the abovementioned (C₃-C₈)-cycloalkyl radicals which is linked via an oxygen or sulfur atom.

“(C₃-C₈)-cycloalkyl-(C₁-C₆)-alkoxy” is, for example, the cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclohexylethoxy or the cyclohexylbutoxy group;

The term “(C₁-C₄)-alkyl-(C₃-C₈)-cycloalkoxy” is, for example, the methylcyclopropyloxy, methylcyclobutyloxy or the butylcyclohexyloxy group.

“(C₁-C₆)-Alkylthio” is an alkylthio group whose hydrocarbon radical has the meaning given under the term “(C₁-C₆)-alkyl”.

Correspondingly, “(C₁-C₆)-alkylsulfinyl” is, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfinyl group and “(C₁-C₆)-alkylsulfonyl” is, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfonyl group.

“(C₁-C₆)-Alkylamino” is a nitrogen atom which is substituted by one or two identical or different alkyl radicals of the above definition.

The term “(C₁-C₆)-mono- or dialkylcarbamoyl” is a carbamoyl group having one or two hydrocarbon radicals which have the meaning given under the term “(C₁-C₆-alkyl)” and which, in the case of two hydrocarbon radicals, may be identical or different.

Correspondingly, “(C₁-C₆)-dihaloalkylcarbamoyl” is a carbamoyl group which carries two (C₁-C₆)-haloalkyl radicals in accordance with the above definition or one (C₁-C₆)-haloalkyl radical and one (C₁-C₆)-alkyl radical in accordance with the above definition.

“(C₁-C₆)-Alkanoyl” is, for example, the acetyl, propionyl, butyryl or 2-methylbutyryl group.

The term “aryl” is to be understood as an isocyclic aromatic radical preferably having 6 to 14, in particular 6 to 12, carbon atoms, such as, for example, phenyl, naphthyl or biphenylyl, preferably phenyl. “Aroyl” is thus an aryl radical as defined above which is attached via a carbonyl group, such as, for example, the benzoyl group.

The term “heterocyclyl” denotes a cyclic radical which may be fully saturated, partially unsaturated or fully unsaturated and which may be interrupted by at least one or more identical atoms from the group nitrogen, sulfur or oxygen, oxygen atoms, however, not being directly adjacent to one another and at least one carbon atom being present in the ring, such as, for example, a thiophene, furan, pyrrole, thiazole, oxazole, imidazole, isothiazole, isoxazole, pyrazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,3,4-triazole, 1,2,4oxadiazole, 1,2,4-thiadiazole, 1,2,4-triazole, 1,2,3-triazole, 1,2,3,4-tetrazole, benzo[b]thiophene, benzo[b]furan, indole, benzo[c]thiophene, benzo[c]furan, isoindole, benzoxazole, benzothiazole, benzimidazole, benzisoxazole, benzisothiazole, benzopyrazole, benzothiadiazole, benzotriazole, dibenzofuran, dibenzothiophene, carbazole, pyridine, pyrazine, pyrimidine, pyridazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,4,5-tetrazine, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, 1,8-naphthyridine, 1,5-naphthyridine, 1,6-naphthyridine, 1,7-naphthyridine, phthalazine, pyridopyrimidine, purine, pteridine 4H-quinolizine; piperidine, pyrrolidine, oxazoline, tetrahydrofuran, tetrahydropyran, isoxazolidine or thiazolidine radical. The term “heteroaromatic” thus embraces, from among the meanings mentioned above under “heterocyclyl”, in each case the fulIly unsaturated aromatic heterocyclic compounds.

“Aryl-(C₁-C₄)-alkoxy” is an aryl radical which is attached via a (C₁-C₄)-alkoxy group, for example the benzyloxy, phenylethoxy, phenylbutoxy or naphthylmethoxy radical.

“Arylthio” is an aryl radical attached via a sulfur atom, for example the phenylthio or the 1- or 2-naphthylthio radical. Correspondingly, “aryloxy” is, for example, the phenoxy or 1- or 2-naphthyloxy radical.

“Aryl-(C₁-C₄)-alkylthio” is an aryl radical which is attached via an alkylthio radical, for example the benzylthio, naphthylmethylthio or the phenylethylthio radical.

The term “(C₁-C₆)-trialkylsilyl” denotes a silicon atom which carries three identical or different alkyl radicals in accordance with the above definition. Correspondingly “aryl-(C₁-C₆)-dialkylsilyl” is a silicon atom which carries one aryl radical and two identical or different radicals in accordance with the above defition, “diaryl-(C₁-C₆)-alkylsilyl” is a silicon atom which carries one alkyl radical and two identical or different aryl radicals in accordance with the above definition, and “triarylsilyl” is a silicon atom which carries three identical or different aryl radicals in accordance with the above definition.

In cases where two or more radicals R¹⁰ are present in a substituent, such as, for example, in -C(═W)NR¹⁰ ₂, these radicals may be identical or different.

Preference is given to those compounds of the formula I in which

Y is C₁-C₆-alkyl which is mono- or polysubstituted by chlorine and/or fluorine;

m is zero;

Q is a 5-membered heterocyclic group

in which

a) X²═NR^(a) and X³═CR^(b)R¹ or

b) X²═CR^(a)R² and X³═CR^(b)R³ or

c) X²═CR⁴R⁵ and X³═CR⁶R⁷;

R^(a) and R^(b) together are a bond;

R¹, R², R³, R⁴ and R⁶ are each independently of one another hydrogen, halogen, C₁-C₁₂-alkyl, C₃-C₈-cycloalkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl, where the four last-mentioned hydrocarbon radicals are optionally mono- or polysubstituted by identical or different radicals from a group A1 consisting of C₁-C₆-alkylcarbonyl, C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino, C₁-C₆-alkylcarbonylamino, C₁-C₆-alkylsulfonylamino, phenyl, furyl, pyrryl, thienyl, halogen, cyano, phenyloxy, phenylthio and phenylamino, where the eleven first-mentioned radicals of group A1 are each optionally mono- or polysubstituted by identical or different radicals from a group B1 consisting of halogen, cyano, C₁-C₃-alkoxy and phenyl which is optionally mono- or polysubstituted by one or more halogen atoms and where the three last-mentioned radicals of group A1 are each optionally mono- or polysubstituted by identical or different radicals from a group B2 consisting of halogen, cyano, nitro, C₁-C₃-alkyl and C₁-C₃-alkoxy, or are C₁-C₆-alkylcarbonyl, C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkoxycarbonyl, phenyl, pyridyl, furyl, thienyl, pyrryl, where the eight last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from group B1, or are OR¹⁰, SR¹⁰ or N(R¹⁰)₂;

R⁵ and R⁷ are each independently of one another hydrogen, halogen, C₁-C₁₂-alkyl, C₃-C₈-cycloalkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl, where the four last-mentioned hydrocarbon radicals are optionally mono- or polysubstituted by identical or different radicals from a group A2 consisting of C₁-C₆-alkylcarbonyl, C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino, C₁-C₆-alkylcarbonylamino, phenyl, furyl, pyrryl, thienyl, halogen, cyano, phenyloxy, phenylthio and phenylamino, where the ten first-mentioned radicals of group A2 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A2 are each optionally mono- or polysubstituted by identical or different radicals from the group B2, or are C₁-C₆-alkylcarbonyl, C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkoxycarbonyl, phenyl, pyridyl, furyl, thienyl, pyrryl, where the eight last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from the group B1, or are OR¹⁰, SR¹⁰ or N(R¹⁰)₂;

R¹⁰ is hydrogen, benzyl, C₁-C₆-alkyl, C₁-C₆-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, phenyl, C₁-C₆-alkylcarbonyl or C₁-C₆-alkylsulfonyl, where the eight last-mentioned radicals are optionally mono- or polysubstituted by identical or different halogen atoms.

Particular preference is given to compounds of the formula I in which

Y is trifluoromethyl;

R¹, R², R³, R⁴ and R⁶ are each independently of one another halogen, C₁-C₁₂-alkyl, C₂-C₁₂-alkenyl, where the two last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from a group A3 consisting of C₁-C₄-alkylcarbonyl, C₁-C₄-alkylaminocarbonyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylamino, C₁-C₄-alkylcarbonylamino, C₁-C₄-alkylsulfonylamino, phenyl, furyl, pyrryl, thienyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, where the eleven first-mentioned radicals of group A3 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A3 are each optionally mono- or polysubstituted by identical or different radicals from the group B2, or are OR¹⁰, SR¹⁰ or N(R¹⁰)₂;

R⁵ and R⁷ are each independently of one another halogen, C₁-C₁₂-alkyl, C₂-C₁₂-alkenyl, where the two last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from a group A4 consisting of C₁-C₄-alkylcarbonyl, C₁-C₄-alkylaminocarbonyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylamino, C₁-C₄-alkylcarbonylamino, phenyl, furyl, pyrryl, thienyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, where the ten first-mentioned radicals of group A4 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A4 are each optionally mono- or polysubstituted by identical or different radicals from the group B2, or are OR¹⁰, SR¹⁰ or N(R¹⁰)₂;

R¹⁰ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, phenyl, C₁-C₄-alkylcarbonyl or C₁-C₄-alkylsulfonyl, where the six last-mentioned radicals are optionally mono- or polysubstituted by identical or different halogen atoms.

Very particular preference is given to compounds of the formula I in which

R¹, R², R³, R⁴ and R⁶ are each independently of one another C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, where the two last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from a group A5 consisting of C₁-C₄-alkylcarbonyl, C₁-C₄-alkylaminocarbonyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylamino, C₁-C₄-alkylcarbonylamino, C₁-C₄-alkylsulfonylamino, phenyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, where the eight first-mentioned radicals of group A5 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A5 are each optionally mono- or polysubstituted by identical or different radicals from the group B2;

R⁵ and R⁷ are each independently of one another C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, where the two last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from a group A6 consisting of C₁-C₄-alkylcarbonyl, C₁-C₄-alkylaminocarbonyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylamino, C₁-C₄-alkylcarbonylamino, phenyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, where the seven first-mentioned radicals of group A6 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A6 are each optionally mono- or polysubstituted by identical or different radicals from the group B2.

Depending on the nature of the substituents defined above, the compounds of the formula (I) have acidic or basic properties and can form salts. If the compounds of the formula (I) carry, for example, groups such as hydroxyl, carboxyl and other groups inducing acidic properties, these compounds can be reacted with bases to give salts. Suitable bases are, for example, hydroxides, carbonates, bicarbonates of the alkali metals and alkaline earth metals, in particular those of sodium, potassium, magnesium and calcium, further ammonia, primary, secondary and tertiary amines having (C₁-C₄)-alkyl radicals and also mono-, di- and trialkanolamines of (C₁-C₄)-alkanols. If the compounds of the formula (I) carry, for example, groups such as amino, alkylamino and other groups inducing basic properties, these compounds can be reacted with acids to give salts. Suitable acids are, for example, mineral acids, such as hydrochloric acid, sulfuric acid and phosphoric acid, organic acids, such as acetic acid, oxalic acid and acidic salts, such as NaHSO₄ and KHSO₄. The salts which can be obtained in this manner likewise have insecticidal, acaricidal and nematicidal properties.

The compounds of the formula (I) may have one or more asymmetric carbon atoms or stereoisomers on double bonds. Enantiomers or diastereomers may therefore be present. The invention embraces both the pure isomers and mixtures thereof. The mixtures of diastereomers can be separated into the isomers by customary methods, for example by selective crystallization from suitable solvents or by chromatography. Racemates can be separated into the enantiomers by customary methods.

The present invention also provides processes for preparing compounds of the formula I:

To prepare compounds of the formula (I) in which

a) X¹═W, X²═NR^(a), X³═CR^(b)R¹ and R^(a), R^(b) and R¹ are as defined above and W is oxygen, activated derivatives of the acid of the formula (II)

where X and Y are as defined above, are reacted in the presence of a base with a compound of the formula (III)

in which the radical R¹ is as defined in formula (I). Suitable activated derivatives are, for example, acyl halides, esters and anhydrides. Suitable bases are amines, such as triethylamine, diisopropylethylamine, pyridine or lutidine, alkali metal hydroxides, alkali metal alkoxides, such as sodium ethoxide or potassium tert-butoxide, or alkylmetal compounds, such as butyllithium.

Depending on the conditions, the reaction described above can be carried out as a one-step process or as a two-step process via intermediates of the formula (IV):

Compounds of the formula (IV) can be cyclized to the 1,2,4-oxadiazoles by heating in an inert solvent at temperatures of up to 180° C.

Compounds of the formula (IV) are also directly obtainable from the acid of the formula (II) and amidoximes of the formula (III) by using a dehydrating reagent such as dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide or N,N′-carbonyidiimidazole.

Both acids of the formula (II) and amidoximes of the formula (III) are commercially available or can be prepared by methods known from the literature (see, for example: Houben-Weyl, Methoden der organischen Chemie, Volume X/4, pages 209-212; EP-A 0 580 374; G. F. Holland, J. N. Pereira, J. Med. Chem., 1967, 10, 149).

In the abovementioned case a) where W is sulfur, the compounds of the formula (I) can be obtained in a manner known from the literature by reaction of a compound of the formula (VII) with an electrophilic amination reagent, such as hydroxylamine-O-sulfonic acid (Y. Lin, S. A. Lang, S. R. Petty, J. Org. Chem. 1980, 45, 3750).

The compounds of the formula (VII) required as starting materials for this reaction can be prepared by reacting the thioamides of the formula (VIII) with dialkylamide dialkyl acetals, of formula (IX), where R¹ is as defined above and R¹² and R¹³ are each C₁-C₄-alkyl.

To prepare compounds of the formula (I) in which

b) X¹═NR^(a), X²═CR^(b)R¹, X³═W and R^(a), R^(b) and R¹ are as defined above, and W is oxygen, amidoximes of the formula (V) can be reacted with activated derivatives of the acids of the formula (VI) or with the acids of the formula (VI) themselves.

To prepare compounds of the formula (I) in which

c) X¹═V, X²═CR^(a)R¹, X³═NR^(b) and R^(a), R^(b) and R¹ are as defined above and V is sulfur, N,N′-diacylhydrazines of the formula (XIII) can be cyclized with a thiolation reagent, such as Lawesson's reagent (A. A. El-Barbary, S. Scheibyl, S. O. Lawesson, H. Fritz, Acta Chem. Scand. 1980, 597), in an inert solvent, such as toluene.

In the abovementioned case b) where W is oxygen, the compounds of the formula (I) can be prepared by reaction of acids of the formula (II) with hydrazines of the formula (X), in which R¹ is as defined above, using an activating reagent, such as phosphorus oxychloride or phosphorus pentachloride.

It is also possible to react acid hydrazides of the formula (XI) with ortho esters of the formula (XII) where R¹ is as defined above, and R¹² is (C₁-C₄)-alkyl.

The reaction can be carried out with or without solvent and with or without an activating reagent. Suitable solvents are hydrocarbons, such as toluene, or ethers, such as 1,2-dimethoxyethane. A suitable activating reagent is, for example, phosphorus oxychloride. The reaction temperature is generally the reflux temperature of the solvent.

To prepare compounds of the formula (I) in which

d) X¹═V, X²═CR^(a)R², X³═CR^(b)R³ and R^(a), R^(b) and R³ are as defined above and V is oxygen, compounds of the formula (XIV) are reacted with a dehydrating reagent.

Suitable dehydrating reagents are inorganic acyl chlorides, such as phosphorus oxychloride or thionyl chloride, inorganic acids, such as sulfuric acid or polyphosphoric acid, or a mixture of phosphoric acid and acetic anhydride (Houben-Weyl, Methoden der organischen Chemie, Volume E8a, pages 935-941). The reaction can be carried out with or without a solvent. Suitable solvents are inert solvents, such as toluene, benzene, dimethoxyethane, dimethylformamide, dimethylacetamide and chlorobenzene. The reaction temperature is advantageously in a range between 50° C. and 150° C.

Compounds of the formula (XIV) can be obtained, for example, by oxidation of the corresponding hydroxyl compound of the formula (XV), it being possible to employ all reagents which are customarily used for this purpose in organic chemistry. (Milos Hudlický, “Oxidations in Organic Chemistry”, ACS Monograph 186, American Chemical Society, Washington, D.C., 1990)

In the abovementioned case d) where V is sulfur, the compounds of the formula (I) can be prepared by condensation of thioamides of the formula (XVII) with carbonyl derivatives of the formula (XVIII), where Z is halogen, in particular chlorine or bromine, acyloxy or sulfonyloxy, in particular methanesulfonyloxy or tolylsulfonyloxy.

To prepare compounds of the formula (I) in which

e) X¹═V, X²═CR⁴R⁵, X³═CR⁶R⁷ and R⁴, R⁵, R⁶ and R⁷ are as defined above and V is oxygen, compounds of the formula (XV) are reacted with cyclization reagents, such as Burgess' reagent (G. M. Atkins, E. M. Burgess, J. Am. Chem. Soc. 1968, 90, 4744.), in a solvent such as tetrahydrofuran and 1,4-dioxane, at a temperature which is in a range between room temperature and the reflux temperature of the solvent.

Compounds of the formual (XV) can be obtained by reacting activated derivatives of the acid in formula (II) with β-aminoalcohols of the formula (XVI), if appropriate in the presence of a base, such as, for example, triethylamine, in an inert solvent, such as, for example, dichlormethane.

An acyl halide or an anhydride can be used as activated derivative of the acid. A number of β-aminoalcohols of the formula (XVI) are commercially available. For others, there is a large number of preparation procedures in the literature, for example a reduction of a-amino acids (B. M. Trost “Comprehensive Organic Synthesis, Reduction”, Volume 8, Pergamon Press, Oxford, 1991). In the abovementioned case e) where V is sulfur, the compounds of the formula (I) can be prepared by reaction of thioamides of the formula (XVII) with compounds of the formula (XIX), the two substituents Z being as defined above and either identical or different (A. R. Katritzky “Comprehensive Heterocyclic Chemistry”, Volume 6, pages 306-312, Pergamon Press, Oxford).

Thioamides of the formula (XVII) are either commercially available or can be obtained by addition of hydrogen sulfide to the corresponding carbonitriles in the presence of a base (A. E. S. Fairfull, J. L. Lowe, D. A. Peak, J. Chem. Soc. 1952, 742).

For preparing compounds of the formula (I) in which

f) X¹═NR^(a), X²═CR^(b)R¹, X³═NR⁸ and R^(a), R^(b), R¹ and R⁸ are as defined above, hydrazides of the formula (XX)

are reacted with a compound of the formula (XXI) or with thioamides of the formula (XXII) (Houben-Weyl, Methoden der organischen Chemie, Volume E8d, pages 510-512).

This reaction can be carried out with or without using a solvent, suitable solvents being alcohols, such as ethanol and propanol, or aromatic hydrocarbons, such as toluene and xylene. If the reaction is carried out in a solvent, the reaction temperature to be chosen is advantageously the reflux temperature of the solvent. If, on the other hand, the reaction is carried out without a solvent, it is possible to heat up to 200° C., if appropriate.

Once the group Q has been assembled, for example by condensation, cyclization or cycloaddition reactions, the radicals R¹ to R⁹ may be derivatized further, if desired, employing the extensive arsenal of methods of organochemical synthesis.

To assemble compounds of the formula (I), in which m is 1, compounds of the formula (I) in which m is 0 can be treated with an oxidizing agent, such as, for example, meta-chloroperbenzoic acid.

The compounds of the formula (I) (also referred to as “active compounds” hereinbelow) have good plant tolerance, favorable homotherm toxicity and advantageous properties with respect to aquatic organisms and are suitable for controlling animal pests, in particular insects, arachnids (Acarina), helminths and molluscs, especially preferably for controlling insects and arachnids which are encountered in agriculture, in animal husbandry, in forests, in the preservation of stored products and materials and in the hygiene sector. They are active against normally sensitive and resistant species and all or individual stages of development. It has to be emphasized that the control of animal pests may be the result both of a toxic action of the compounds according to the invention and of a deterrant (repellant) action. The abovementioned pests include: From the order of the Acarina, for example, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp. and Eutetranychus spp.

From the order of the Isopoda, for example, Oniscus asselus, Armadium vulgar and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus and Scutigera spp.

From the order of the Symphyla, for example, Scutigerella immaculate.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Blatta orientalis, Periplaneta americana, Leucophaea madeirae, Blatella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Schistocerca gregaria.

From the order of the Isoptera, for example, Reticulitermes spp. From the order of the Anoplura, for example, Phylloera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. and Linognathus spp.

From the order of the Mallophaga, for example, Trichodectes spp. and Damalinea spp.

From the order of the Thysanoptera, for example, Hercinothrips femoralis, Thrips tabaci and Frankliniella spp.

From the order of the Heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis spp., Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelus bilobatus, Nephotettix cincticeps, Lecanium comi, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psylla spp.

From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrelIa, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonelIa, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanimna, Tortrix viridana, Cuaphalocrocis spp. and Manduca spp.

From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylloides chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonumus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrynchus assimilis, Hypera postica, Dermestes spp., Trogoderma, Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica and Lissorhoptus spp.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hypobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Tipula paludosa.

From the order of the Siphonaptera, for example, Xenopsylla cheopsis and Ceratophyllus spp.

From the order of the Arachnida, for example, Scorpio maurus and Latrodectus mactans.

From the class of helminths, for example, Haemonchus, Trichostrongulus, Ostertagia, Cooperia, Chabertia, Strongyloides, Oesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Heterakis, as well as Fasciola.

From the class of Gastropoda, for example, Deroceras spp., Arion spp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., Bulinus spp. and Oncomelania spp.

From the class of Bivalva, for example, Dreissena spp.

The phytoparasitic nematodes which can be controlled according to the invention include, for example, the root-parasitic soil nematodes, such as, for example, those of the genera Meloidogyne (root gall nematodes, such as Meloidogyne incognita, Meloidogyne hapla and Meloidogyne javanica), Heterodera and Globodera (cyst-forming nematodes, such as Globodera rostochiensis, Globodera pallida and Heterodera trifolii) and of the genera Radopholus (such as Radopholus similis), Pratylenchus (such as Pratylenchus neglectus, Pratylenchus penetrans and Pratylenchus curvitatus), Tylenchulus (such as Tylenchulus semipenetrans), Tylenchorhynchus (such as Tylenchorhynchus dubius and Tylenchorhynchus claytoni), Rotylenchus (such as Rotylencus robustus), Heliocotylenchus (such as Heliocotylenchus multicinctus), Belonoaimus (such as Belonoaimus longicaudatus), Longidorus (such as Longidorus elongatus), Trichodorus (such as Trichodorus primitivus) and Xiphinema (such as Xiphinema index).

The nematode genera Ditylenchus (stem parasites, such as Ditylenchus dipsaci and Ditylenchus destructor), Aphelenchoides (leaf nematodes, such as Aphelenchoides ritzemabosi) and Anguina (blossom nematodes, such as Anguina tritici) can furthermore be controlled with the compounds according to the invention.

The invention also relates to compositions, in particular insecticidal and acaricidal compositions, which comprise the compounds of the formula (I) in addition to suitable formulation auxiliaries.

The compositions according to the invention in general comprise the active compounds of the formula (1) to the extent of 1 to 95% by weight. They can be formulated in various ways, depending on how this is determined by the biological and/or chemico-physical parameters. Suitable formulation possibilities are therefore:

Wettable powders (WP), emulsifiable concentrates (EC), aqueous solutions (SL), emulsions, sprayable solutions, oil- or water-based dispersions, suspension concentrates (SC), suspoemulsions (SE), dusting powders (DP), seed dressings, granules in the form of microgranules, sprayed granules, absorption granules and adsorption granules, water-dispersible granules (WG), ULV formulations, microcapsules, waxes or baits.

These individual types of formulation are known in principle and are described, for example, in: Winnacker-Kuchler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Edition 1986; van Falkenberg, “Pesticides Formulations”, Marcel Dekker N.Y., 2nd Edition 1972-73; K. Martens, “Spray Drying Handbook”, 3rd Edition 1979, G. Goodwin Ltd. London.

The necessary formulation auxiliaries, i.e. carrier substances and surface-acting substances, such as inert materials, surfactants, solvents and further additives, are likewise known and are described, for example, in: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd Edition, Darland Books, Caldwell N.J.; H. v. Olphen, “Introduction to Clay Colloid Chemistry”, 2nd Edition, J. Wiley & Sons, N.Y.; Marsden, “Solvents Guide”, 2nd Edition, lnterscience, N.Y. 1950; McCutcheon's, “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Schonfeldt, “Grenzflachenaktive Athylenoxidaddukte” [Surface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1967; Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Edition 1986.

Combinations with other substances having a pesticidal action, fertilizers and/or growth regulators can be prepared on the basis of these formulations, for example in the form of a ready-to-use formulation or as a tank mix. Wettable powders are preparations which are uniformly dispersible in water and which, alongside the active compound, and in addition to a diluent or inert substance, also comprise wetting agents, for example polyethoxylated alkylphenols, polyethoxylated fatty alcohols or alkyl- or alkylphenol-sulfonates, and dispersing agents, for example sodium ligninsulfonate or sodium 2,2′-dinaphthylmethane6,6′-disulfonate. Emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or also higher-boiling aromatics or hydrocarbons, with the addition of one or more emulsifiers. Emulsifiers which can be used are, for example: calcium alkylarylsulfonates, such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.

Dusting powders are obtained by grinding the active compound with finely divided solid substances, for example talc, naturally occurring clays, such as kaolin, bentonite and pyrophillite, or diatomaceous earth. Granules can be prepared either by spraying the active compound onto granular inert material capable of adsorption or by applying active compound concentrates to the surface of carrier substances, such as sand, kaolinites or granular inert material, by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or mineral oils. Suitable active compounds can also be granulated in the manner customary for the preparation of fertilizer granules—if desired as a mixture with fertilizers.

In wettable powders, the active compound concentration is generally about 10 to 90% by weight, the remainder to make up 100% by weight comprising customary formulation constituents. In emulsifiable concentrates, the active compound concentration can be about 5 to 80% by weight. Dust-like formulations usually comprise 5 to 20% by weight of active compound, and sprayable solutions about 2 to 20% by weight. In granules, the content of active compound partly depends on whether the active compound is present in liquid or solid form and what granulating auxiliaries, fillers and the like are used.

In addition, the active compound formulations mentioned comprise, if appropriate, the particular customary tackifiers, wetting agents, dispersing agents, emulsifiers, penetration agents, solvents, fillers or carriers.

For use, the concentrates in the commercially available form are diluted in the customary manner, if appropriate, for example by means of water in the case of wettable powders, emulsifiable concentrates, dispersions and in some cases also microgranules. Dust-like and granular formulations as well as sprayable solutions are usually not diluted further with additional inert substances before use.

The required amount applied varies with external conditions, such as temperature, humidity and the like. It can vary within wide limits, for example between 0.0005 and 10.0 kg/ha or more of active substance, but is preferably between 0.001 and 5 kg/ha.

The active compounds according to the invention can be present in their commercially available formulations and in the use forms prepared from these formulations as mixtures with other active compounds, such as insecticides, attractants, sterilizing agents, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.

The pest control agents include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, formamidines, tin compounds, substances produced by microorganisms and the like.

Preferred partners for the mixtures are

1. from the group of phosphorus compounds acephate, azamethiphos, azinphos-ethyl-, azinphosmethyl, bromophos, bromophos-ethyl, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, demeton, demeton-S-methyl, demeton-S-methyl sulfone, dialifos, diazinon, dichlorvos, dicrotophos, O,O-1,2,2,2-tetrachloroethyl phosphorthioate (SD 208 304), dimethoate, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitriothion, fensulfothion, fenthion, fonofos, formothion, heptenophos, isozophos, isothioate, isoxathion, malathion, methacrifos, methamidophos, methidathion, salithion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosfolan, phosmet, phosphamidon, phoxim, pirimiphos, primiphos-ethyl, pirimiphos-methyl, profenofos, propaphos, proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos, suiprofos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorphon, vamidothion;

2. from the group of carbamates aldicarb, 2-sec-butylphenyl methylcarbamate (BPMC), carbaryl, carbofuran, carbosulfan, cloethocarb, benfuracarb, ethiofencarb, furathiocarb, isoprocarb, methomyl, 5-methyl-m-cumenyl butyryl(methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, ethyl 4,6,9-triaza-4-benzyl-6, 10-dimethyl8-oxa-7-oxo-5, 11-dithia-9-dodecenoate (OK 135), 1-methylthio(ethylideneamino) N-methyl-N-(morpholinothio)carbamate (UC 51717);

3. from the group of carboxylic acid esters allethrin, alphametrin, 5-benzyl-3-furylmethyl (E)-(1 R)-cis, 2,2-di-methyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, bioallethrin, bioallethrin ((S)-cyclopentyl isomer), bioresmethrin, biphenate, (RS)-1-cyano-1-(6-phenoxy-2-pyridyl)methyl (1RS)-trans-3-(4-tert-butylphenyl)-2,2-dimethylcyclopropanecarboxylate (NCI 85193), cycloprothrin, cyhalothrin, cythithrin, cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D isomer), permethrin, pheothrin ((R) isomer), d-pralethrin, pyrethrins (naturally occurring products), resmethrin, tefluthrin, tetramethrin and tralomethrin;

4. from the group of amidines amitraz, chlordimeform;

5. from the group of tin compounds cyhexatin, fenbutatin oxide;

6. others abamectin, Bacillus thuringiensis, bensultap, binapacryl, bromopropylate, buprofezin, camphechlor, cartap, chlorobenzilate, chlorfluazuron, 2-(4-chlorophenyl)-4,5-diphenylthiophene (UBI-T 930), chlorfentezine, 2-naphthylmethyl cyclopropanecarboxylate (Ro 12-0470), cyromazin, N-(3,5-dichloro4-(1,1,2,3,3,3-hexafluoro-1-propyloxy)phenyl)carbamoyl)-2-chlorobenzocarboximide acid ethyl ester, dicofol, N-(N-(3,5-i-chloro4-(1,1,2,2-tetrafluoroethoxy)phenylamino)carbonyl)-2,6-difluorobenzamide (XRD 473), diflubenzuron, N-(2,3-dihydro-3-methyl-1,3-thiazol-2-ylidene)-2,4-xylidene, dinobuton, dinocap, endosulfan, ethofenprox, (4-ethoxyphenyl)(dimethyl)(3-(3-phenoxyphenyl)propyl)silane, (4-ethoxyphenyl)(3-(4-fluoro-3-phenoxyphenyl)propyl)dimethylsilane, fenoxycarb, 2-fluoro-5-(4-(4-ethoxyphenyl)4-methyl-1-pentyl)diphenyl ether (MTI 800), granulosis and nuclear polyhedrosis viruses, fenthiocarb, flubenzimine, flucycloxuron, flufenoxuron, gamma-HCH, hexythiazox, hydramethyinon (AC 217300), ivermectin, 2-nitromethyl4,5-dihydro-6H-thiazine (DS 52618), 2-nitromethyl-3,4-dihydrothiazole (SD 35651), 2-nitromethylene-1,2-thiazinan-3-ylcarbamaldehyde (WL 108477), propargite, teflubenzuron, tetradifon, tetrasul, thiocyclam, trifumuron, imidacloprid.

The abovementioned combination partners are known active compounds, and most of them are described in Ch. R. Worthing, S. B. Walker, The Pesticide Manual, 7th Edition (1983), British Crop Protection Council.

The active compound content of the use forms prepared from the commercially available formulations can be from 0.00000001 to 95% by weight of active compound, preferably between 0.00001 and 1 % by weight.

The active compounds are used in a customary manner appropriate for the use forms.

The active compounds according to the invention are also suitable for controlling endo- and ectoparasites in the veterinary medicine field and in the field of animal husbandry. The active compounds according to the invention are used here in a known manner, such as by oral use in the form of, for example, tablets, capsules, potions or granules, by means of dermal use in the form of, for example, dipping, spraying, pouring-on, spotting-on and dusting, and by parenteral use in the form of, for example, injection.

The novel compounds of the formula (I) can accordingly also particularly advantageously be used in livestock husbandry (for example cattle, sheep, pigs and poultry, such as chickens, geese and the like). In a preferred embodiment of the invention, the compounds are administered orally to the animals, if appropriate in suitable formulations (cf. above) and if appropriate with the drinking water or feed. Since excretion in the faeces takes place in an active manner, the development of insects in the faeces of the animals can be prevented very easily in this way. The dosages and formulations suitable in each case depend in particular on the species and the development stage of the stock animals and also on the pressure of infestation, and can easily be determined and specified by the customary methods. The novel compounds can be employed in cattle, for example, in dosages of 0.01 to 1 mg/kg of body weight.

In addition to the application methods mentioned hereinabove, the active compounds of the formula I according to the invention also have excellent systemic action. The active compounds can therefore also be introduced into the plants via below-ground and above-ground parts of plants (root, stem, leaf), when the active compounds are applied in liquid or solid form to the immediate surroundings of the plants (for example granules in soil application, application in flooded rice fields).

Furthermore, the active compounds according to the invention are particularly useful for treating vegetative and generatative propagation stock, such as, for example, seed of, for example, cereals, vegetables, cotton, rice, sugar beet and other crops and ornamentals, of bulbs, cuttings and tubers of other vegetatively propagated crops and ornamentals. To this end, treatment can be carried out prior to sowing or planting (for example by special seed coating techniques, by seed dressings in liquid or solid form or by seed box treatment), during sowing or planting or after sowing or planting by special application techniques (for example seed row treatment). Depending on the application, the amount of active compound applied can vary within a relatively wide range. In general, the application rates are between 1 g and 10 kg of active compound per hectare of soil area.

The examples below serve to illustrate the invention.

A. Formulation examples

a) A dusting powder is obtained by mixing 10 parts by weight of active compound and 90 parts by weight of talc, as the inert substance, and comminuting the mixture in an impact mill.

b) A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of acitve compound, 65 parts by weight of kaolin-containing quartz, as the inert substance, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleoylmethyltauride, as wetting and dispersing agent and grinding the mixture in a pinned disk mill.

c) A dispersion concentrate which is readily dispersible in water is prepared by mixing 40 parts by weight of active compound with 7 parts by weight of a sulfosuccinic monoester, 2 parts by weight of a sodium ligninsulfonate and 51 parts by weight of water and grinding the mixture to a fineness of below 5 microns in a grinding bead mill.

d) An emulsifiable concentrate can be prepared from 15 parts by weight of active compound, 75 parts by weight of cyclohexane, as the solvent, and 10 parts by weight of ethoxylated nonylphenol (10 EO), as the emulsifier.

e) Granules can be prepared from 2 to 15 parts by weight of active compound and an inert granule carrier material, such as attapulgite, pumice granules and/or quartz sand. A suspension of the wettable powder from Example b) having a solids content of 30% is expediently used, and this is sprayed onto the surface of attapulgite granules and the components are dried and mixed intimately. The weight content of the wettable powder is approximately 5% and that of the inert carrier material is approximately 95% of the finished granules.

B. Chemical examples

Example No. 1

3-Isopropyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4oxadiazole (Table 1, No. 81)

2 g of methyl 4-trifluoromethylnicotinate and 1.56 g of isobutyramide oxime were initially charged in 15 ml of ethanol and cooled to 0° C. 10 ml of a 1.2 molar sodium ethoxide solution were added dropwise to this solution. The mixture was allowed to warm to room temperature over a period of two hours and stirring was then continued at this temperature until the reaction, according to TLC, had ended. The reaction mixture was concentrated and the residue was taken up in saturated ammonium chloride solution and extracted with diethyl ether. Chromatographic purification of the crude product gave the desired compound as a yellowish oil. ¹H-NMR (CDCl₃, 300 MHz): d =1.41 (d, J=6.9 Hz, 6H), 3.22 (m, 1H), 7.78 (d, J=5 Hz, 1H), 9.02 (d, J=5 Hz, 1H), 9.34 (s, 1H) ppm.

Example No. 2

3-lsopropyl-5-(4-tifluoromethyl-5pydmidyl)-1,2,4-oxadiazole (Table 1, No. 189)

2 g of ethyl 4-trifluoromethylpyrimidine-5-carboxylate and 1.56 g of isobutyramide oxime were intiially charged in 15 ml of ethanol and cooled to 0° C. 10 ml of a 1.2 molar sodium ethoxide solution were added dropwise to this solution. The mixture was allowed to warm to room temperature over a period of one hour and then heated under reflux until the reaction, according to TLC, had ended. The reaction mixture was concentrated and the residue was taken up in saturated ammonium chloride solution and extracted with diethyl ether. Chromatographic purification of the crude product gave the desired compound as a yellowish oil. ¹H-NMR (CDCl₃, 300 MHz): d =1.43 (d, J=7 Hz, 6H), 3.22 (hept., J=7 Hz, 1H), 9.52 (s, 1H), 9.58 (s, 1H) ppm.

Example No. 3

2-Methyl-5-(4-trfluoromethyl-3-pyridyl)-1,3,4-oxadiazole (Table 3, No. 549)

500 mg of 4-trifluoromethyinicotinic hydrazide were heated under reflux in 3.5 ml of triethyl orthoacetate for 2 hours. The reaction mixture was subsequently concentrated and the residue was carefully admixed with 2 ml of phosphorus oxychloride. The mixture was stirred at room temperature for 1 hour and then poured on ice and extracted with ethyl acetate. Chromatographic purification of the crude product obtained after drying and concentrating gave the desired compound as a yellowish oil.

¹H-NMR (CDCl₃, 300 MHz): d =2.67 (s, 3H), 7.75 (d, J=5 Hz, 1H), 8.99 (d, J=5 Hz, 1H), 9.34 (s, 1H) ppm.

Example No. 4

4-(Ethoxycarbonylmethyl)-2-(4-tifluoromethyl-3-pyridyl)thiazole (Table 4, No. 688)

500 mg of 4-trifluoromethylpyridine-3-thiocarboxamide and 440 mg of ethyl 4-chloroacetate were dissolved in 5 ml of dimethylformamide and heated at 100° C. for 4 hours. After cooling, the reaction mixture was poured onto ice-water and extracted with diethyl ether. The diethyl ether phase was dried (MgSO₄), filtered and concentrated and the residue was purified by chromatography. This gave the desired product in pure form as a colorless oil.

¹H-NMR (CDCl₃, 300 MHz): d =1.28 (t, J=7.5 Hz, 3H), 3.92 (s, 2H), 4.22 (q, J=7.5 Hz, 2H), 7.43 (s, 1H), 7.68 (d, J=5 Hz, 1H), 8.86 (d, J=5 Hz, 1H), 8.97 (s, 1H) ppm.

Example No. 5:

4-Ethyl-2-(4-tnfluoromethyl-3-pyndyl)oxazole (Table 4, No. 762)

2.6 g of 4-trifluoromethylnicotinic acid were admixed with 20 ml of thionyl chloride and heated at reflux temperature for 1 hour. After cooling, excess thionyl chloride was distilled off and the acyl chloride which remained as a pale yellow oil was taken up in 30 ml of dichloromethane. This solution was subsequently added dropwise to a solution of 2.4 9 of 2-amino-i-butanol and 2.75 g of triethylamine in 30 ml of dichloromethane cooled in an ice bath. After the addition had ended, stirring was continued at room temperature for approximately 2 hours. The mixture was poured into ammonium chloride solution and extracted with ethyl acetate. The crude N-(1-hydroxy-2-butyl)-4-trifluoromethyinicotinamide (2.3 g) obtained after drying and concentrating the ethyl acetate phase was dissolved at room temperature in 100 ml dichloromethane and mixed with 4.6 g of periodinan (Dess-Martin reagent). After the reaction had ended, according to TLC, the reaction mixture was concentrated and purified by column chromatography. The resulting 2-(trifluoromethylpyridin-3-amido)butanal (1.5 g) was dissolved in 30 ml of dimethylformamide, admixed with 2.72 g of phosphorus oxychloride and heated at 90° C. for 15 minutes. The solution was then poured onto ice and extracted with diethyl ether. Drying and concentration of the diethyl ether phase and chromatographic purification of the residue gave the product as a brownish oil.

¹H-NMR (CDCl₃, 300 MHz): d =1.3 (t, J=7.4 Hz, 3H), 2.66 (qd, J=7.4 Hz, J<1 Hz, 2H), 7.58 (t, J<1 Hz, 1H), 7.65 (d, J 5 Hz, 1H), 8.83 (d, J=5 Hz, 1H), 9.33 (d, J=5 Hz, 1H) ppm.

Example No. 6

4-Ethyl-2-(4-trifiuoromethyl-3-pyridyl)-4,5 dihydrooxazole (Table 5, No 876)

1 g of 4-trifluoromethylnicotinic acid was admixed with 8 ml of thionyl chloride and heated at reflux temperature for 1 hour. After cooling, excess thionyl chloride was distilled off and the acyl chloride which remained as a pale yellow oil was taken up in 10 ml of dichloromethane. This solution was subsequently added dropwise to a solution of 930 mg of 2-amino-1-butanol and 1.06 9 of triethylamine in 10 ml of dichloromethane cooled in an ice bath. After the addition had ended, stirring was continued for approximately 2 hours at room temperature. The mixture was poured into an ammonium chloride solution and extracted with ethyl acetate. The crude N-(1-hydroxy-2-butyl)-4-trifluoromethyinicotinamide (1.03 g) obtained after drying and concentration of the ethyl acetate phase was dissolved at room temperature in 6 ml of tetrahydrofuran and admixed with 1.09 g of N-[(triethylammonio)sulfonyl]-methylcarbamate (Burgess' reagent). The mixture was stirred at 60° C. for 3 hours. After cooling, the batch was concentrated and the residue was taken up in water and extracted with ethyl acetate. Chromatographic purification of the crude product gave the product as a colorless oil.

¹H-NMR (CDCl₃, 200 MHz): d =1.03 (t, J=7.6 Hz, 3H), 1.72 (m, 2H), 4.15 (t, J=7.5 Hz, 1H), 4.32 (m, 1H), 4.58 (t, J=7.5 Hz, 1H), 7.6 (d, J=5 Hz, 1H), 8.87 (d, J=5 Hz, 1H), 9.06 (s, 1H) ppm.

Example No. 7

2-(3-Thienylmethyl)-5(4-tifluoromethyl-3-pyidyl)-1,3,4-oxadiazole (Table 3, No. 572)

880 mg of thiophene-3-acetic hydrazide were added to a solution of 960 mg of 4-trifluoromethylpyridine-3-carboxylic acid in 5 ml of phosphorus oxychloride, and the mixture was heated at reflux for 2 hours. The reaction mixture was subsequently added dropwise to ice-water, made neutral using concentrated ammonia solution and extracted with ethyl acetate. Drying (Na₂SO₄), concentration and chromatographic purification gave 624 mg of the desired product as a slightly brown oil.

¹H-NMR (CDCl₃, 200 MHz): d =4.38 (s, 2H), 7.1 (d, J=5 Hz, 1H), 7.23 (s, 1H), 7.37 (dd, J=5 Hz, J=3 Hz, 1H), 7.75 (d, J=6 Hz,₁H), 8.98 (d, J=6 Hz, 1H), 9.36 (s, 1H) ppm.

Example No. 8

5Methyl-3-(4-trifluoromethyl-3-pyridyl)-1H-1,2,4-triazole (Table 6, No. 947)

A mixture of 290 mg of ethylacetimidate hydrochloride and 100 mg of sodium hydroxide in 2 ml of ethanol was filtered and added to 500 mg of 4-trifluoromethyl-3-pyridinecarbohydrazide, and the mixture was heated under reflux for 3 hours. The reaction mixture was concentrated and the residue was suspended in xylene and refluxed for 4 hours. For work-up, the batch was diluted with ethyl acetate and washed with water. Chromatographic purification gave the pure product as a colorless solid.

¹H-NMR (CDCl₃, 300 MHz): d =2.58 (s, 3H), 7.64 (d, J=5 Hz,1H), 8.85 (d, J=5 Hz, 1H), 9.19 (s, 1H) ppm.

Example 9

3-(N-Isopropylcarbamoylmethyl)-5-(4-trfluoromethyl-3-pyridyl)-1,2,4-oxadiazole

Step 1: Tert-butyl 3-amino-3-(4-trifluoromethyl-3-pyridinecarbonyloxy-imino)propionate

30 g of 4-trifluoromethyl-3-pyridinecarboxylic acid is initially charged in 150 ml of dry THF and, a little at a time, admixed with 25.3 9 of carbonyl-diimidazole. The mixture is stirred at room temperature for 30 min. 27.2 g of tert-butoxycarbonylacetamide oxime dissolved in 150 ml of THF are then added dropwise. The mixture is stirred overnight, the solvent is evaporated and the residue is taken up in ethyl acetate, washed three times with 1 M sulfuric acid and once with saturated sodium bicarbonate solution. Concentration of the ethyl acetate phase gives 28 g of the product as a pale yellow solid.

¹H-NMR (CDCl₃, 300MHz): d =1.5 (s, 9H), 3.3 (s, 2H), 5.55 (br.s, 2H), 7.83 (d, J=5 Hz, 1H), 8.97 (d, J=5 Hz, 1H), 9.13 (s, 1H) ppm.

Step 2: 3-(Tert-butoxycarbonylmethyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

28 g of tert-butyl 3-amino-3-(4-trifluoromethyl-3-pyridinecarbonyloxy-imino)propionate are dissolved in 380 ml of toluene and heated under reflux for 17 hours. Concentration and chromatographic purification of the residue over silica gel gives 14.4 g of the product as a pale brown oil.

¹H-NMR (CDCl₃, 300MHz): d =1.5 (s, 9H), 3.88 (s, 2H), 7.79 (d, J=5 Hz, 1H), 9.02 (d, J=5 Hz, 1H), 9.33 (s, 1H) ppm.

Step 3: 3-(Hydroxycarbonylmethyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

12.4 g of 3-(tert-butoxycarbonylmethyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole are dissolved in 110 ml of dichloromethane and admixed with 57 ml of trifluoroacetic acid. The reaction mixture is stirred at room temperature for 1.5 hours and subsequently concentrated under reduced pressure. The residue is repeatedly taken up in dichloromethane and reconcentrated to remove any remaining trifluoroacetic acid. The mixture is finally triturated with diethyl ether, giving 8.1 g of the product as a white solid.

Step 4: 3-(N-Isopropylcarbamoylmethyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

1 g of the product of the previous step are dissolved in 10 ml of THF and is mixed with 0.59 g of carbonyldiimidazole. The mixture is stirred at room temperature for 10 minutes, 0.22 g of isopropylamine are added dropwise and the mixture is allowed to react for a further 1.5 hours at room temperature with stirring. The reaction mixture is subsequently concentrated and the residue is taken up in ethyl acetate and washed three times with 1 M sulfuric acid and once with saturated sodium bicarbonate solution. The solid residue obtained after drying and concentrating the ethyl acetate phase is recrystallized from tert-butyl methyl ether, giving 0.46 g of the pure product as a pale yellow solid.

¹H-NMR (CDCl₃, 300 MHz): d =1.20 (d, J=7.6 Hz, 6H), 3.82 (s, 2H), 4.12 (m, 1H), 6.50 (br.s, 1H), 7.81 (d, J=5 Hz, 1H), 9.02 (d, J=5 Hz, 1H), 9.37 (s, 1H) ppm.

Example No. 10

3-(N,N-Dimethylaminocarbamoyl)-5-(4-tiifiuoromethyl-3-pyridyl)-1,2,4-oxadiazole (Table 1, No. 502)

Step 1: Ethyl 2-amino-2-(4-trifluoromethyl-3-pyridinecarbonyloxyimino)acetate

17.3 g of carbonyidiimidazole are initially charged in 200 ml of 1,4-dioxane and, a little at a time, admixed with 20 g of 4-trifluoromethyl-3-pyridinecarboxylic acid. The mixture is stirred at room temperature for 1 h and subsequently heated to 45° C. for 2 h. After cooling to 30° C., 14.5 g of ethoxycarbonylformamide oxime are added and the mixture is stirred at 45° C. for 3 h. The precipitated solid is filtered off with suction and the filtrate is concentrated to 50 ml and, together with the solid, added to 250 ml of ice-water. The solid is filtered off with suction and dried at 50° C. under reduced pressure. This gives 28.7 9 of the product as a white solid of mp. 172-174° C.

Step 2: 3-Ethoxycarbonyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole

20 g of ethyl 2-amino-2-(4-trifluormethyl-3-pyridinecarbonyloxyimino)-acetate are dissolved in 200 ml of a mixture of xylene and toluene and admixed with 5 g of Amberlyst 15. The mixture is boiled at 125-130° C. for 6 h using a Dean-Stark apparatus. After the reaction has ended, the mixture is cooled and admixed with a small amount of diethyl ether. The mixture is filtered with suction through a glass filter frit, and the solution is then concentrated. This gives 15.8 g of the product as a yellow oil.

Step 3: 5-(4-Trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole-3-carboxylic acid

15.8 g of 3-ethoxycarbonyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole are initially charged in 13 ml of methanol, and, with ice-cooling at 0° C., a solution of 2.8 g of lithium hydroxide in 50 ml of water is added dropwise. The mixture is stirred at room temperature for 2 h, 20 ml of ice-water are added and the mixture is extracted with 200 ml of diethyl ether. The aqueous phase is adjused to pH═2 using dil. HCl, and the precipitated product is filtered off with suction. After drying, 13.8 g of 5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole-3-carboxylic acid are obtained as a white solid of mp. 157-159° C.

Step 4: N,N-Dimethyl-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole-3-carboxamide

5.8 g of carbonyldiimidazole are initially charged in 90 ml of tetrahydrofuran and, a little at a time, admixed with 9 g of 5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole-3-carboxylic acid. The mixture is stirred at room temperature for 15 min and then heated at 50° C. for 2 h. After cooling to room temperature, 2.3 g of dimethylamine are introduced in a very gentle gas stream over a period of 2 h. After a reaction time of 12 h, the mixture is concentrated and taken up in 200 ml of diethyl ether. The mixture is washed with ice-cold half conc. hydrochloric acid solution, washed neutral with sat. sodium bicarbonate sol., dried over magnesium sulfate and concentrated under reduced pressure. This gives a slightly yellow oil which solidifies after a number of days to a solid of mp. 52-54° C.

In a similar manner, it is possible to prepare the compounds shown in Tables 1 to 6 below.

The abbreviations used denote

Ph: phenyl THP: 2-tetrahydropyranyl

TABLE 1

No. X Y m W R¹ m.p. [° C.] 1 N CCl₃ 0 O CH₃ 2 N CCl₃ 0 O CH₂CH₃ 3 N CCl₃ 0 O COOCH₂CH₃ 4 CH CCl₃ 0 O CH₃ 5 CH CCl₃ 0 O COOCH₂CH₃ 6 N (CF₂)₃CHCF₂ 0 O CH₃ 7 N (CF₂)₃CHCF₂ 0 O COOCH₂CH₃ 8 CH (CF₂)₃CHCF₂ 0 O CH₃ 9 CH (CF₂)₃CHCF₂ 0 O COOCH₂CH₃ 10 N (CF₂)₃CHCF₂ 0 S CH₂COOC(CH₃₎ ₃ 11 N (CF₂)₃CHCF₂ 0 S CH₂CONHCH₃ 12 CH (CF₂)₃CHCF₂ 0 S (CH₂)₂CH₃ 13 CH (CF₂)₃CHCF₂ 0 S COOCH₂CH₃ 14 N (CF₂)₂CHCF₂ 0 O CH₂CH₃ 15 N (CF₂)₂CHCF₂ 0 O COOCH₂CH₃ 16 N (CF₂)₂CHCF₂ 0 O OH 17 N (CF₂)₂CHCF₂ 0 O OCH₃ 18 CH (CF₂)₂CHCF₂ 0 O CH₃ 19 CH (CF₂)₂CHCF₂ 0 O COOCH₂CH₃ 20 CH (CF₂)₂CHCF₂ 0 O OH 21 CH (CF₂)₂CHCF₂ 0 O NHCH₃ 22 N CF₂CF₃ 0 O CH₃ 23 N CF₂CF₃ 0 O CH₂CH₃ 24 N CF₂CF₃ 0 O (CH₂)₂CH₃ 25 N CF₂CF₃ 0 O CH(CH₃)₂ 26 N CF₂CF₃ 0 O Cyclo-C₆H₁₁ 27 N CF₂CF₃ 0 O CH₂C═CH₂ 28 N CF₂CF₃ 0 O CH₂C≡CH 29 N CF₂CF₃ 0 O CH₂CH₂C≡CH 30 N CF₂CF₃ 0 O CH₂C≡CCH₂CH₃ 31 N CF₂CF₃ 0 O (CH₂)₄C≡CH 32 N CF₂CF₃ 0 O CHFCF₃ 33 N CF₂CF₃ 0 O COOCH₂CH₃ 34 N CF₂CF₃ 0 O CH₂COOC(CH₃)₃ 35 N CF₂CF₃ 0 O CH₂CONHCH₃ 36 N CF₂CF₃ 0 O NH₂ 37 N CF₂CF₃ 0 O NHCH₂CH₃ 38 CH CF₂CF₃ 0 O CH₃ 39 CH CF₂CF₃ 0 O CH₂CH₃ 40 CH CF₂CF₃ 0 O (CH₂)₂CH₃ 41 CH CF₂CF₃ 0 O CH(CH₃)₂ 42 CH CF₂CF₃ 0 O Cyclo-C₆H₁₁ 43 CH CF₂CF₃ 0 O CH₂C═CH₂ 44 CH CF₂CF₃ 0 O CH₂COOC(CH₃)₃ 45 CH CF₂CF₃ 0 O NH₂ 46 CH CF₂CF₃ 0 O NHCOCH₃ 47 CH CF₂CF₃ 0 O NHCOCH₂CH₃ 48 N CF₂CF₃ 0 S CH₃ 49 N CF₂CF₃ 0 S CH₂CH₃ 50 N CF₂CF₃ 0 S (CH₂)₂CH₃ 51 N CF₂Cl 0 O CH₃ 52 N CF₂Cl 0 O CH₂CH₃ 53 N CF₂Cl 0 O (CH₂)₂CH₃ 54 N CF₂Cl 0 O CH(CH₃)₂ 55 N CF₂Cl 0 O CH₂COOC(CH₃)₃ 56 N CF₂Cl 0 O CH₂CONHCH₃ 57 N CF₂Cl 0 O OH 58 N CF₂Cl 0 O OCH₃ 59 N CF₂Cl 0 O OCH₂CH₃ 60 N CF₂Cl 0 O NHCH₃ 61 CH CF₂Cl 0 O CH₃ 62 CH CF₂Cl 0 O CH₂CH₃ 63 CH CF₂Cl 0 O (CH₂)₂CH₃ 64 CH CF₂Cl 0 O CH(CH₃)₂ 65 CH CF₂Cl 0 O CH₂COOC(CH₃)₃ 66 CH CF₂Cl 0 O CH₂CONHCH₃ 67 CH CF₂Cl 0 O OH 68 CH CF₂Cl 0 O OCH₃ 69 CH CF₂Cl 0 O OCH₂CH₃ 70 CH CF₂Cl 0 O NHCH₃ 71 CH CF₂Cl 0 O Cyclo-C₆H₁₁ 72 CH CF₂Cl 0 O CH₂C═CH₂ 73 CH CF₂Cl 0 O COOCH₂CH₃ 74 CH CF₂Cl 0 O CH₂COOC(CH₃)₃ 75 CH CF₂Cl 0 O CH₂CONHCH₃ 76 CH CF₂Cl 0 O OCH₃ 77 CH CF₂Cl 0 O NHCH₃ 78 CH CF₃ 0 O CH₃ oil 79 CH CF₃ 0 O CH₂CH₃ oil 80 CH CF₃ 0 O (CH₂)₂CH₃ oil 81 CH CF₃ 0 O CH(CH₃)₂ oil 82 CH CF₃ 0 O Cyclo-C₃H₅ oil 83 CH CF₃ 0 O (CH₂)₃CH₃ oil 84 CH CF₃ 0 O CH(CH₃)CH₂CH₃ oil 85 CH CF₃ 0 O CH₂CH(CH₃)₂ oil 86 CH CF₃ 0 O C(CH₃)₃ oil 87 CH CF₃ 0 O Cyclo-C₄H₇ 88 CH CF₃ 0 O (CH₂)₄CH₃ oil 89 CH CF₃ 0 O CH(CH₃)(CH₂)₂CH₃ 90 CH CF₃ 0 O (CH₂)₂CH(CH₃)₂ 91 CH CF₃ 0 O CH₂C(CH₃)₃ 92 CH CF₃ 0 O Cyclo-C₅H₉ oil 93 CH CF₃ 0 O (CH₂)₅CH₃ 94 CH CF₃ 0 O O(CH₂CH₃)₂CH₃ 95 CH CF₃ 0 O Cyclo-C₆H₁₁ 96 CH CF₃ 0 O (CH₂)₆CH₃ 97 CH CF₃ 0 O CH(CH₃)(CH₂)₄CH₃ 98 CH CF₃ 0 O Cyclo-C₇H₁₃ 99 CH CF₃ 0 O CH₂-cyclo-C₆H₁₁ 100 CH CF₃ 0 O 2-Norbornyl 101 CH CF₃ 0 O (CH₂)₇CH₃ 102 CH CF₃ 0 O CH(CH₂CH₃)(CH₂)₅CH₃ 103 CH CF₃ 0 O (CH₂)₈CH₃ 104 CH CF₃ 0 O (CH₂)₃-cyclo-C₆H₁₁ 105 CH CF₃ 0 O (CH₂)₉CH₃ 106 CH CF₃ 0 O 1-Adamantyl 107 CH CF₃ 0 O (CH₂)₁₀ CH₃ 108 CH CF₃ 0 O (CH₂)₁₁CH₃ 109 CH CF₃ 0 O CH(CH₃)(CH₂)₉CH₃ 110 CH CF₃ 0 O (CH₂)₁₂CH₃ 111 CH CF₃ 0 O (CH₂)₁₃CH₃ 112 CH CF₃ 0 O (CH₂)₁₄CH₃ 113 CH CF₃ 0 O (CH₂)₁₅CH₃ 114 CH CF₃ 0 O (CH₂)₁₇CH₃ 115 CH CF₃ 0 O (CH₂)₁₉CH₃ 116 CH CF₃ 0 O CHO 117 CH CF₃ 0 O CH═CH₂ oil 118 CH CF₃ 0 O CH₂C═C(CH₃)₂ 119 CH CF₃ 0 O CH₂CH₂C═CH₂ 120 CH CF₃ 0 O CH₂C═CH₂ 121 CH CF₃ 0 O C(CH₃)═CH₂ 122 CH CF₃ 0 O (E)-CH₂CH═CHCH₂CH₃ 123 CH CF₃ 0 O (Z)-CH₂CH═CHCH₂CH₃ 124 CH CF₃ 0 O (CH₂)₅C═CH₂ 125 CH CF₃ 0 O C(═CHCH₃)CH₃ 62-64 126 CH CF₃ 0 O Geranyl 127 CH CF₃ 0 O 3-Menthyl 128 CH CF₃ 0 O C≡CH 129 CH CF₃ 0 O CH₂C≡CH 130 CH CF₃ 0 O CH₂CH₂C≡CH 131 CH CF₃ 0 O CH₂CH₂C≡CH 132 CH CF₃ 0 O (CH₂)₄C≡CH 133 CH CF₃ 0 O CHFCF₃ oil 134 CH CF₃ 0 O COOCH₂CH₃ oil 135 CH CF₃ 0 O CH₂CH₂OH oil 136 CH CF₃ 0 O CH₂CH₂OCH₃ oil 137 CH CF₃ 0 O CH₂COOC(CH₃)₃ oil 138 CH CF₃ 0 O CH₂SC₆H₅ oil 139 CH CF₃ 0 O CH₂CONHCH₃ 109-111 140 CH CF₃ 0 O CH₂CH(CH)CH₂OH 141 CH CF₃ 0 O CH₂COCH₃ 142 CH CF₃ 0 O COCH₃ 143 CH CF₃ 0 O CH₂OC₆H₅ 144 CH CF₃ 0 O COC₆H₅ 145 CH CF₃ 0 O CO(4-Cl)-C₆H₄ 146 CH CF₃ 0 O CF₂CH₃ 147 CH CF₃ 0 O CH₂CN 148 CH CF₃ 0 O CH₂CH₂CN 149 CH CF₃ 0 O CH₂CH(—O—)CH₂ 150 CH CF₃ 0 O CH₂(4-OCH₃)C₆H₅ 151 CH CF₃ 0 O CH₂-cyclo-(4-Oxo)-C₆H₈ 152 CH CF₃ 0 O CH₂CH(CH)CH₂SC₆H₅ 153 CH CF₃ 0 O CH₂CH₂Si(CH₃)₃ 154 CH CF₃ 0 O CH═CF₂ 155 CH CF₃ 0 O CCl═CHCl 156 CH CF₃ 0 O 2-Pyridyl  99-101 157 CH CF₃ 0 O 2-Furyl 158 CH CF₃ 0 O 2-Thienyl 106-108 159 CH CF₃ 0 O CH₂C≡CCH₂CH₂OTHP 160 CH CF₃ 0 O CH₂CH₂Cl oil 161 CH CF₃ 0 O Si(CH₃)₃ 162 CH CF₃ 0 O OC₆H₅ 163 CH CF₃ 0 O OH 164 CH CF₃ 0 O OCH₃ 165 CH CF₃ 0 O OCH₂CH₃ 166 CH CF₃ 0 O OCHF₂ 167 CH CF₃ 0 O OCH₂C₆H₅ 168 CH CF₃ 0 O CH₂SCH₃ 48-49 169 CH CF₃ 0 O SC₆H₅ 170 CH CF₃ 0 O SeC₆H₅ 171 CH CF₃ 0 O NH₂ 116-118 172 CH CF₃ 0 O NHCH₃ 173 CH CF₃ 0 O NHCH₂CH₃ 174 CH CF₃ 0 O N(CH₂CH₃)₂ 175 CH CF₃ 0 O CONHCH₂C═CH₂ 105-107 176 CH CF₃ 0 O Cl 177 CH CF₃ 0 O Br 178 CH CF₃ 0 O CONH₂ 206-208 179 CH CF₃ 0 O NHCOCH₃ 129-131 180 CH CF₃ 0 O NHCOCH₂CH₃ 181 CH CF₃ 0 O OSO₂CH₃ 182 CH CF₃ 0 O SOCH₂(4-Br)—C₆H₄ 183 CH CF₃ 0 O N(CH₃)COOCH₂C₆H₅ 184 CH CF₃ 0 O NHNH₂ 185 CH CF₃ 0 O NHN(CH₃)₂ 186 N CF₃ 0 O CH₃ 187 N CF₃ 0 O CH₂CH₃ oil 188 N CF₃ 0 O (CH₂)₂CH₃ oil 189 N CF₃ 0 O CH(CH₃)₂ oil 190 N CF₃ 0 O (CH₂)₃CH₃ oil 191 N CF₃ 0 O CH₂CH(CH₃)₂ oil 192 N CF₃ 0 O C(CH₃)₃ 193 N CF₃ 0 O (CH₂)₄CH₃ oil 194 N CF₃ 0 O CH(CH₃)(CH₂)₂CH₃ 195 N CF₃ 0 O CH₂C(CH₃)₃ 196 N CF₃ 0 O Cyclo-C₅H₉ 197 N CF₃ 0 O (CH₂)₅CH₃ 198 N CF₃ 0 O Cyclo-C₆H₁₁ 199 N CF₃ 0 O CH(CH₃)(CH₂)₄CH₃ 200 N CF₃ 0 O CH₂-cyclo-C₆H₁₁ 201 N CF₃ 0 O (CH₂)₇CH₃ 202 N CF₃ 0 O (CH₂)₈CH₃ 203 N CF₃ 0 O (CH₂)₉CH₃ 204 N CF₃ 0 O CH(CH₃)(CH₂)₉CH₃ 205 N CF₃ 0 O (CH₂)₁₅CH₃ 206 N CF₃ 0 O (CH₂)₁₇CH₃ 207 N CF₃ 0 O (CH₂)₁₉CH₃ 208 N CF₃ 0 O CH₂CH═C(CH₃)₂ 209 N CF₃ 0 O CH₂CH₂CH═CH₂ 210 N CF₃ 0 O CH₂CH═CH₂ 211 N CF₃ 0 O (Z)-CH₂CH═CHCH₂CH₃ 212 N CF₃ 0 O (CH₂)₅CH═CH₂ 213 N CF₃ 0 O CH₂C≡CH 214 N CF₃ 0 O CH₂C≡CCH₂CH₃ 215 N CF₃ 0 O CHFCF₃ 216 N CF₃ 0 O COOCH₂CH₃ 217 N CF₃ 0 O CH₂CH₂OH 218 N CF₃ 0 O CH₂CH₂OCH₃ 219 N CF₃ 0 O CH₂COOC(CH₃)₃ 220 N CF₃ 0 O CH₂SC₆H₅ 221 N CF₃ 0 O CH₂CONHCH₃ 222 N CF₃ 0 O CH₂CH(CH)CH₂OH 223 N CF₃ 0 O CHO 224 N CF₃ 0 O COCH₃ 225 N CF₃ 0 O CH₂OC₆H₅ 226 N CF₃ 0 O COC₆H₅ 227 N CF₃ 0 O CF₂CH₃ 228 N CF₃ 0 O CH₂CN 229 N CF₃ 0 O CH₂CH₂CN 230 N CF₃ 0 O CH═CF₂ 231 N CF₃ 0 O 2-Furyl 232 N CF₃ 0 O CH₂C≡C—I 233 N CF₃ 0 O OH 234 N CF₃ 0 O OCH₃ 235 N CF₃ 0 O OCH₂CH₃ 236 N CF₃ 0 O OCHF₂ 237 N CF₃ 0 O OCH₂C₆H₅ 238 N CF₃ 0 O SC₆H₅ 239 N CF₃ 0 O NH₂ 240 N CF₃ 0 O NHCH₃ 241 N CF₃ 0 O NHCH₂CH₃ 242 N CF₃ 0 O N(CH₂CH₃)₂ 243 N CF₃ 0 O N(CH₂CN)₂ 244 N CF₃ 0 O N(CH₃)₂ 245 N CF₃ 0 O NHCOCH₃ 246 N CF₃ 0 O NHCOCH₂CH₃ 247 N CF₃ 0 O OSO₂CH₃ 248 N CF₃ 0 O NHNH₂ 249 CH CF₃ 0 S CH₃ 250 CH CF₃ 0 S CH₂CH₃ 251 CH CF₃ 0 S (CH₂)₂CH₃ 252 CH CF₃ 0 S CHO 253 CH CF₃ 0 S CHFCF₃ 254 CH CF₃ 0 S CH₂C≡CH 255 CH CF₃ 0 S COOCH₂CH₃ 256 CH CF₃ 0 S CH₂COOC(CH₃)₃ 257 CH CF₃ 0 S CH₂CN 258 CH CF₃ 0 S SeC₆H₅ 259 N CF₃ 0 S CH₃ 260 N CF₃ 0 S CH₂CH₃ 261 N CF₃ 0 S (CH₂)₂CH₃ 262 N CF₃ 0 S CHFCF₃ 263 N CF₃ 0 S CH₂CH₂OH 264 N CF₃ 0 S CH₂COOC(CH₃)₃ 265 CH CH₂CH₂Cl 0 O CH₃ 266 CH CH₂CH₂Cl 0 O CH₂CH₃ 267 CH CH₂CH₂Cl 0 O (CH₂)₂CH₃ 268 CH CH₂CH₂Cl 0 O CH(CH₃)₂ 269 CH CH₂CH₂Cl 0 O CH₂SC₆H₅ 270 CH CH₂CH₂Cl 0 O CH₂CONHCH₃ 271 CH CH₂CH₂Cl 0 O NH₂ 272 CH CH₂CH₂Cl 0 O NHCH₂CH₃ 273 N CH₂CH₂Cl 0 O CH₂CH₃ 274 N CH₂CH₂Cl 0 O NH₂ 275 N CH₂Cl 0 O CH₃ 276 CH CH₂Cl 0 O CH₃ 277 CH CHF₂ 0 O CH₃ 278 CH CHF₂ 0 O CH₂CH₃ 279 CH CHF₂ 0 O (CH₂)₂CH₃ 280 CH CHF₂ 0 O CH₂CH═CH₂ 281 CH CHF₂ 0 O C(CH₃)═CH₂ 282 CH CHF₂ 0 O COOCH₂CH₃ 283 CH CHF₂ 0 O CH₂CONHCH₃ 284 CH CHF₂ 0 O CF₂CH₃ 285 CH CHF₂ 0 O CHO 286 CH CHF₂ 0 O NH₂ 287 CH CHF₂ 0 O Cl 288 CH CHF₂ 0 O NHCOCH₃ 289 CH CHF₂ 0 O NHNH₂ 290 N CHF₂ 0 O CH₃ 291 N CHF₂ 0 O CH₂CH₃ 292 N CHF₂ 0 O CH(CH₃)(CH₂)₄CH₃ 293 N CHF₂ 0 O CH₂CH═CH₂ 294 N CHF₂ 0 O COOCH₂CH₃ 295 N CHF₂ 0 O NH₂ 296 CH CF₃ 1 O CH₃ 297 CH CF₃ 1 O COOCH₂CH₃ 298 CH CF₃ 1 O CH₂COOC(CH₃)₃ 299 CH CF₃ 1 O CHFCF₃ 300 N CF₃ 0 O CH₂NHSO₂CH₃ 301 N CF₃ 0 O (CH₂)₂NHSO₂CH₃ 302 N CF₃ 0 O CH₂NHSO₂CH₂CH₃ 303 N CF₃ 0 O CH₂NHSO₂CH₂C₆H₅ 304 CH CF₃ 0 O (CH₂)₄NHSO₂CF₃ 305 CH CF₃ 0 O (CH₂)₂S(CH₂)₂CH₃ 306 CH CF₃ 0 O (CH₂)₄S(CH₂)₄OCH₃ 307 CH CF₃ 0 S (CH₂)₂S(CH₂)₂CN 308 CH CF₃ 0 S CH₂NHSO₂CH₂CH₃ 309 CH CF₃ 0 S CH₂NHSO₂CH₂C₆H₅ 310 CH CF₃ 0 S (CH₂)₂NHSO₂CH₃ 311 CH CF₃ 0 S CH₂NHSO₂CH₃ 312 CH CF₃ 0 S OH(CH₃)CH₂NHC₆H₅ 313 CH CF₃ 0 S (CH₂)₂S(2-F)—C₆H₄ 314 CH CF₃ 0 S (CH₂)₆NHCH₂)₆OCH₃ 315 CH CF₃ 0 S (CH₂)₂NH-(2-F)—C₆H₄ 316 CH CF₃ 0 S (CH₂)₃NHCH₂CN 317 CH CF₃ 0 S (CH₂)₂O(3-Cl)—C₆H₄ 318 CH CF₃ 0 S (CH₂)₆NHCH₂CF₃ 319 CH CF₃ 0 S (CH₂)₂O(3-CH₃)—C₆H₄ 320 CH CF₃ 0 O CH₂NHC₆H₅ 321 CH CF₃ 0 O (CH₂)₄S(2-Br)—C₆H₄ 322 CH CF₃ 0 O (CH₂)₆NH(CH₂)₂OCH₃ 323 CH CF₃ 0 O (CH₂)₂NH(CH₂)₄OCH₃ 324 CH CF₃ 0 O (CH₂)₃NH-(4-CN)—C₆H₄ 325 CH CF₃ 0 O (CH₂)₂O(3-CH₃)—C₆H₄ 326 CH CF₃ 0 O (CH₂)₄NHCH₂CF₃ 327 CH CF₃ 0 O (CH₂)₄NHCH₂CN 328 CH CF₃ 0 O (CH₂)₃O(4-OCH₃)—C₆H₄ 329 CH CF₃ 0 O CH₂SO₂-tert-C₄H₉ oil 330 CH CF₃ 0 O CH₂SO₂-(4-F)—C₆H₄ oil 331 CH CF₃ 0 O CH₂SO₂—C₆H₅ oil 332 CH CF₃ 0 O CH₂SOCH₃ 63 333 CH CF₃ 0 O CH₂SO—C₆H₅ oil 334 CH CF₃ 0 O CH₂CONH(CH₂)₂CH₃ 80-82 335 CH CF₃ 0 O (4-OCF₃)—C₆H₄ 57-59 336 CH CF₃ 0 O CH₂OCH₃ oil 337 CH CF₃ 0 O

53-54 338 CH CF₃ 0 O

oil 339 CH CF₃ 0 O CH₂CH₂OCH₂CH₃ oil 340 CH CF₃ 0 O CH₂CH₂NC₆H₅ 80-83 341 CH CF₃ 0 O

80-81 342 CH CF₃ 0 O

110-111 343 CH CF₃ 0 O CH₂CH₂O(CO)-(4-Cl)—C₆H₄ 80-82 344 CH CF₃ 0 O CH₂-(4-OCH₃)—C₆H₄ 54-55 345 CH CF₃ 0 O CH₂-(3-Cl)—C₆H₄ 51-52 346 CH CF₃ 0 O CH₂-cyclo-C₃H₅ oil 347 CH CF₃ 0 O CH₂-(4-C₆H₅)—C₆H₄ oil 348 CH CF₃ 0 O

143-144 349 CH CF₃ 0 O CH₂CH₂O(CO)-(2,6-F2)-C₆H₃ 57-58 350 CH CF₃ 0 O CH₂CH₂O(CO)-(4-NO₂)—C₆H₄ 80-81 351 CH CF₃ 0 O CH₂-(2,6-Cl₂)—C₆H₃ 91-92 352 CH CF₃ 0 O CH₂CH₂OSO₂CH₃ oil 353 CH CF₃ 0 O CH₂CH₂O(CO)-tert-C₄H₉ oil 354 CH CF₃ 0 O CH₂-(3-F)—C₆H₄ 50-51 355 CH CF₃ 0 O CH₂CONCH₂C≡CH 129-131 356 CH CF₃ 0 O CH₂CH₂O(CO)-cyclo-C₃H₇ oil 357 CH CF₃ 0 O CH₂CH₂O(CO)CH₃ oil 358 CH CF₃ 0 O CH₂-[2,4-(CH₃)₂]—C₆H₃ 85-86 359 CH CF₃ 0 O CH₂CONCH₂CH═CH₂ 210-212 360 CH CF₃ 0 O CH₂CON(CH₂CH₃)₂ oil 361 CH CF₃ 0 O CH₂CON(CH₂)₃CH₃ 77-79 362 CH CF₃ 0 O CH₂CONCH₂-(2-furyl) 139-141 363 CH CF₃ 0 O CH₂CONCH(CH₃)₂ 112-114 364 CH CF₃ 0 O CH₂CONCH(CH₃)[(CH₂)₄CH₃] 73-75 365 CH CF₃ 0 O CH₂CONCH₂CH₂C₆H₅ 120-122 366 CH CF₃ 0 O CH₂CONCH₂CH₂OCH₂CH₃ 78 367 CH CF₃ 0 O CH₂CONCH₂CF₃ 176-178 368 CH CF₃ 0 O CH₂CONCH(CH₃)[(CH₂)₅CH₃] 85-86 369 CH CF₃ 0 O

oil 370 CH CF₃ 0 O

oil 371 CH CF₃ 0 O CH₂CH2-(1-pyrryl) oil 372 CH CF₃ 0 O CH₂CH₂C₆H₅ oil 373 CH CF₃ 0 O CH₂Cl 53-54 374 CH CF₃ 0 O (CH₂)₃OH 38-39 375 CH CF₃ 0 O CH₂CONCH(CH₃)[(CH₂)₂]CH₃ 68-69 376 CH CF₃ 0 O CH₂CH(OCH₃)₂ oil 377 CH CF₃ 0 O CH₂CONCH₂C(CH₃)₃ oil 378 CH CF₃ 0 O CH₂CONC(CH₃)₂(CH₂CH₃) oil 379 CH CF₃ 0 O CH₂CONCH₂CH₂-cyclo-C₆H₁₁ 82-85 380 CH CF₃ 0 O CH₂CONCH(CH₃)(1-naphthyl) 142-146 381 CH CF₃ 0 O (CH₂)₃Cl oil 382 CH CF₃ 0 O CH₂CON-tert-C₄H₉ oil 383 CH CF₃ 0 O CH₂CON(iso-C₃H₇)₂ 70-72 384 CH CF₃ 0 O CH₂CON(CH₂)₇CH₃ 79-81 385 CH CF₃ 0 O CH₂CON-cyclo-C₆H₁₁ 119-121 386 CH CF₃ 0 O CH₂CONCH₂CH₂-(4-Cl)—C₆H₄ 120-121 387 CH CF₃ 0 O CH₂CONCH₂-(2-thienyl) 137-139 388 CH CF₃ 0 O

151-153 389 CH CF₃ 0 O CH₂CONHCH(CH₃)(CH₂CH₃) 87-89 390 CH CF₃ 0 O (CH₂)₃SCH₃ oil 391 CH CF₃ 0 O (CH₂)₃SOCH₃ oil 392 CH CF₃ 0 O CH₂CONC(CH₃)₂(C≡CH) 111-113 393 CH CF₃ 0 O CH₂CONCH(CH₃)CH₂CH₂CH 72-74 (CH₃)₂ 394 CH CF₃ 0 O

oil 395 CH CF₃ 0 O CH₂CON-cyclo-C₅H₉ 110-112 396 CH CF₃ 0 O CH₂CON(CH₂)₄CH₃ 75-77 397 CH CF₃ 0 O

190-192 398 CH CF₃ 0 O CH₂CON(3-CF₃)C₆H₄ 136-138 399 CH CF₃ 0 O CH₂CON-cyclo-C₈H₁₇ 115-117 400 CH CF₃ 0 O

oil 401 CH CF₃ 0 O CH₂CON-Adamantyl oil 402 CH CF₃ 0 O CH₂CON(CH₂CH₂CH₃)₂ oil 403 CH CF₃ 0 O CH₂CONCH(CH₃)[(4-F)-C₆H₄] 111-113 404 CH CF₃ 0 O CH₂CONCH₂CH(CH₃)₂ 91-93 405 CH CF₃ 0 O

Oil 406 CH CF₃ 0 O CH₂CONCH₂CH₂OC₆H₅  99-101 407 CH CF₃ 0 O CH₂CH═NOCH₃ oil 408 CH CF₃ 0 O CH₂CONCH₂CH₂-[3,4- 123-125 (OCH₃)₂]C₆H₃ 409 CH CF₃ 0 O CH₂CON-(2-Cl)C₆H₄ 138-140 410 CH CF₃ 0 O CH₂CON-(2-SCH₃)C₆H₄ 136-138 411 CH CF₃ 0 O

222-225 412 CH CF₃ 0 O

207-209 413 CH CF₃ 0 O CH₂CON-(3-Br)C₆H₄ 129-131 414 CH CF₃ 0 O CH₂CON—N-(2,4,6-Cl₃)C₆H₂ 153-155 415 CH CF₃ 0 O CH₂CON-(4-I)C₆H₄ 143-145 416 CH CF₃ 0 O CH₂CON—NCOCH₂(3-Thienyl) 185-187 417 CH CF₃ 0 O CH₂CH₂CHO oil 418 CH CF₃ 0 O CH₂CON(CH₃)[(CH₂)₃CH₃] oil 419 CH CF₃ 0 O CH₂CON-(3,5-Cl₂-2,4-F₂)C₆H 166-167 420 CH CF₃ 0 O CH₂CON—C₆H₅ 215-217 421 CH CF₃ 0 O CH₂CON(CH₃)(C₆H₁₁₎ oil 422 CH CF₃ 0 O CH₂CON(CH₂CH₃)(CH₂CH═CH₂) oil 423 CH CF₃ 0 O CH₂CON(CH₂CH₃)[CH(CH₃)₂] oil 424 CH CF₃ 0 O CH₂CONCH(CH₃)[(CH₃)₂] 108-110 425 CH CF₃ 0 O CH₂CON(CH₂CH₃)[CH₂C(═CH₂) oil (CH₃)] 426 CH CF₃ 0 O CH₂CONCH₂(4-tert-C₄H₉)C₆H₄ oil 427 CH CF₃ 0 O CH₂CONCH(CH₃)(tert-C₄H₉) oil 428 CH CF₃ 0 O CH₂CONCH(CH₃[CH₂CH(CH₃)( oil CH₂CH₃)] 429 CH CF₃ 0 O CH₂CONCH₂COOCH₂CH₃ 103-105 430 CH CF₃ 0 O CH₂CON[(CH₂)₂CH₃](CH₂-cyclo- oil C₃H₇) 431 CH CF₃ 0 O CH₂CONCH(CH₃)CH₂CH₂CH 80-82 (CH₃)₂ 432 CH CF₃ 0 O CH₂CONCH(CH₂CH₃)[CH₂CH oil (CH₃)₂] 433 CH CF₃ 0 O CH₂C═O-(1-Piperidinyl) oil 434 CH CF₃ 0 O

180-182 435 CH CF₃ 0 O CH₂CONCH₂C(═CH2)(CH₃) 86-87 436 CH CF₃ 0 O CH₂CONCH[CH(CH₃)₂](COO oil CH₃) 437 CH CF₃ 0 O CH₂CONCH₂-cyclo-C₃H₇ oil 438 CH CF₃ 0 O CH₂CON(CH₂)₅OH oil 439 CH CF₃ 0 O CH₂CON(CH₃)(CH₂CO₂CH₃) oil 440 CH CF₃ 0 O CH₂CON(CH₃)(CH₂CN) oil 441 CH CF₃ 0 O CH₂CONCH[CH₂CH(CH₃)₂](CO₂ oil CH₃₎ 442 CH CF₃ 0 O CH₂CON-(1-Piperidinyl) oil 443 CH CF₃ 0 O CH₂CONCH₂CH₂OCH₃ 97-99 444 CH CF₃ 0 O CH₂CH₂SC₆H₅ oil 445 CH CF₃ 0 O CH₂CH₂SCH₃ oil 446 CH CF₃ 0 O CH₂CH₂SCH₂C₆H₅ oil 447 CH CF₃ 0 O

oil 448 CH CF₃ 0 O CH₂CON-(2-OH)C₆H₄ 162-164 449 CH CF₃ 0 O CH₂CON-(3-OH)C₆H₄ oil 450 CH CF₃ 0 O CH₂CON-(2-CH₃)C₆H₄ 163-164 451 CH CF₃ 0 O CH₂CON-(3-NO₂)C₆H₄ 176-178 452 CH CF₃ 0 O CH₂CON-(3-OCF₂CHFCl)C₆H₄ 120-121 453 CH CF₃ 0 O CH₂CON-(3-CF₃-4-F)C₆H₃ 168-170 454 CH CF₃ 0 O CH₂CON-(2,4-Cl₂)C₆H₃ 120-122 455 CH CF₃ 0 O CH₂CON-(2-F-4.Cl)C₆H₃ 148-151 456 CH CF₃ 0 O CH₂CON-[2,4-(CH₃)₂]C₆H₃ 123-125 457 CH CF₃ 0 O CH₂CON-[2,3-(CH₃)₂]C₆H₃ waxy 458 CH CF₃ 0 O

waxy 459 CH CF₃ 0 O CH₂CON-(2-CH₃-3-Cl)C₆H₃ 160-162 460 CH CF₃ 0 O CH₂CON(CH₂CH₃)(C₆H₅₎ oil 461 CH CF₃ 0 O

124-126 462 CH CF₃ 0 O CH₂CON(2-OCH₃-5-Ph)C₆H₃ 167-169 463 CH CF₃ 0 O

157-158 464 CH CF₃ 0 O CH₂CON-(3-NO₂-4-Cl)C₆H₃ oil 465 CH CF₃ 0 O CH₂CON-(2-Cl-4-CH₃)C₆H₃ 106-108 466 CH CF₃ 0 O CH₂CON-(3-OCH₂CH₃)C₆H₄ waxy 467 CH CF₃ 0 O

169-171 468 CH CF₃ 0 O CH₂CON-(4-CH₃)C₆H₄ 139-141 469 CH CF₃ 0 O CH₂CON-(1-Naphthyl) 155-157 470 CH CF₃ 0 O CH₂CON-(3-I)C₆H₄ 135-137 471 CH CF₃ 0 O CH₂CON-(2-OCH₂CH₃)C₆H₄ 138 472 CH CF₃ 0 O CH₂CON-(2-OCH₃)C₆H₄ 130-132 473 CH CF₃ 0 O CH₂CON-[3,5-(OCH₃)₂]C₆H₃ 130-132 474 CH CF₃ 0 O CH₂CON-(4-Cl)C₆H₄ 139-141 475 CH CF₃ 0 O CH₂CON-(3-CH₃)C₆H₄ oil 476 CH CF₃ 0 O CH₂CON-(3-OCH₃)C₆H₄ oil 477 CH CF₃ 0 O CH₂CON-(4-CH₂CH₃)C₆H₄ 122-123 478 CH CF₃ 0 O CH₂CON-(4-CF₃)C₆H₄ 151-152 479 CH CF₃ 0 O CH₂CON-(2-CH₃-4-Cl)C₆H₃ 165-167 480 CH CF₃ 0 O CH₂CH₂NCH₂C₆H₅ oil 481 CH CF₃ 0 O CH₂CH₂NCH₂-(3-Pyridyl) oil 482 CH CF₃ 0 O CH₂CH═NOCH₂CH₃ oil 483 CH CF₃ 0 O CH₂CH═NOC₆H₅ oil 484 CH CF₃ 0 O CH₂CON-(4-NO₂)C₆H₄ 181-183 485 CH CF₃ 0 O CH₂CON-(2-CH₃-4-NO2)C₆H₃ 129-131 486 CH CF₃ 0 O CH₂CON-(2-Cl-3-CF₃)C₆H₃ 136 487 CH CF₃ 0 O CH₂CON-(2-CN-4-Cl)C₆H₃ 157-159 488 CH CF₃ 0 O CH₂CON-(3,5-Cl₂)C₆H₃ 167-169 489 CH CF₃ 0 O CH₂CON-(3,5-Cl₂-4- 132-134 OCF₂CHF₂)C₆H₂ 490 CH CF₃ 0 O CH₂CON-(2,4,5-Cl₃)C₆H₂ 146 491 CH CF₃ 0 O CH₂CON-(3,5-Cl₂-4- 124-126 OCF₂CHFCF₃)C₆H₂ 492 CH CF₃ 0 O CH₂CON-(2-CF₃-4-Cl)C₆H₃ 136 493 CH CF₃ 0 O

oil 494 CH CF₃ 0 O

91-93 495 CH CF₃ 0 O

123-125 496 CH CF₃ 0 O

81-83 497 CH CF₃ 0 O

113-115 498 CH CF₃ 0 O COOH 155-157 499 CH CF₃ 0 O 4-F-C₆H₄ 104-106 500 CH CF₃ 0 O CON(C₂H₅)₂ oil 501 CH CF₃ 0 O CONCH(CH₃)₂ oil 502 CH CF₃ 0 O CON(CH₃)₂ 52-54 503 CH CF₃ 0 O CONHCH₂CCH 105-107 504 CH CF₃ 0 O CONH-cyclo-C₃H₅ 101-103 505 CH CF₃ 0 O CONH₂ 206-208 506 CH CF₃ 0 O

72-74 507 CH CF₃ 0 O

 98-100 508 CH CF₃ 0 O

108-110 509 CH CF₃ 0 O

140-142 510 CH CF₃ 0 O CONHCH₃ 127-129 511 CH CF₃ 0 O CONHCH₂CH═CH₂ oil 512 CH CF₃ 0 O CON(CH₂CN)₂ 90-92 513 CH CF₃ 0 O 4-(t-C₄H₉)-C₆H₄ 64-66 514 CH CF₃ 0 O 4-CF₃-C₆H₄ 89-91 515 CH CF₃ 0 O 4-CH₃-3-F-C₆H₃ 104-106 516 CH CF₃ 0 O 2,4-di-Cl—C₆H₃ 70-72 517 CH CF₃ 0 O 4-(NHSO₂CH₃)—C₆H₄ 204-206 518 CH CF₃ 0 O 2,6-di-Cl-C₆H₃ 139-141 519 CH CF₃ 0 O COOCH₂C₆H₅ 83-85 520 CH CF₃ 0 O CONHC₃H₇ oil 521 CH CF₃ 0 O 3,5-di-Br-4-(OCH₃)—C₆H₂ 132-134 522 CH CF₃ 0 O CHCl₂ oil 523 CH CF₃ 0 O CCl₃ oil 524 CH CF₃ 0 O CH(OCH3)₂ oil 525 CH CF₃ 0 O 3-CF₃—C₆H₄ 57-59 526 CH CF₃ 0 O CON(CH₂)₅ oil 527 CH CF₃ 0 O CON(CH₃)CH₂C₆H₅ oil 528 CH CF₃ 0 O CONHCH₂C₆H₅ 96-98 529 CH CF₃ 0 O

oil 530 CH CF₃ 0 O CONH-n-C₆H₁₃ oil 531 CH CF₃ 0 O CON(CH₂CH₃)CH₂C₆H₅ oil 532 CH CF₃ 0 O CONH-c-C₆H₁₁ 115-117 533 CH CF₃ 0 O CON(n-C₄H₉)₂ oil 534 CH CF₃ 0 O

oil 535 CH CF₃ 0 O CONH-i-C₄H₉ oil 536 CH CF₃ 0 O

oil 537 CH CF₃ 0 O CON(CH₂)₄ 68-70 538 CH CF₃ 0 O CON(CH₃)-n-C₆H₁₃ oil 539 CH CF₃ 0 O

oil 540 CH CF₃ 0 O CON(CH₃)CH₂CH₃ oil 541 CH CF₃ 0 O CONHOCH₃ oil 542 CH CF₃ 0 O

oil 543 CH CF₃ 0 O CON(CH₃)CH₂CH₂CH₃ oil 544 CH CF₃ 0 O CONHCH₂CH(OCH₃)₂ oil 545 CH CF₃ 0 O CONH-t-C₄H₉ 113-115 546 CH CF₃ 0 O CONHCH₂-4-Cl-C₆H₄ oil 547 CH CF₃ 0 O CONHCH(CH₃)C₆H₅ oil 548 CH CF₃ 0 O CONHCH₂CH₂OCH₃ 92-94 549 CH CF₃ 0 O

190-192 550 CH CF₃ 0 O CONHC(CH₃)₂CCH 90-92 551 CH CF₃ 0 O CONHCH₂-2-Furyl 93-95 552 CH CF₃ 0 O CON(CH₂)₃ 91-93 553 CH CF₃ 0 O CONHCH₂-c-C₃H₅ oil 554 CH CF₃ 0 O CONHC(CH₃)₂CH₂CH₃ oil 555 CH CF₃ 0 O CONH(CH₂)₃C₆H₅ oil 556 CH CF₃ 0 O CONHCH₂-3-Pyridyl 132-134 557 CH CF₃ 0 O CON(CH₃)-n-C₄H₉ oil 558 CH CF₃ 0 O CON(CH₂CH3)-i-C₃H₇ oil 559 CH CF₃ 0 O

oil 560 CH CF₃ 0 O CONHCH₂CH₂Cl oil 561 CH CF₃ 0 O CONHCH₂CN 152-157 562 CH CF₃ 0 O CON(CH₃)OCH₃ oil 563 CH CF₃ 0 O CON(CH₃)CH₂CH═CH₂ oil 564 CH CF₃ 0 O CONHCH₂COOCH₃ oil 565 CH CF₃ 0 O CON(CH₃)-i-C₃H₇ oil 566 CH CF₃ 0 O CON(CH₃)CH₂CH₂CN oil 567 CH CF₃ 0 O CON(CH₃)CH₂CH(OCH₃)₂ oil 568 CH CF₃ 0 O CON(CH₃)CH₂CH(—CH₂CH₂O—) oil 569 CH CF₃ 0 O CONHCH₂C(═CH₂)CHH₃ oil 570 CH CF₃ 0 O CON(CH₂CH₃)CH₂CH═CH₂ oil 571 CH CF₃ 0 O CONHC₆H₅ 83-85 572 CH CF₃ 0 O CON(CH₃)CH₂CCH oil 573 CH CF₃ 0 O CON(CH₃)CH₂CN oil 574 CH CF₃ 0 O CON(CH₃)CH₂CH₂N(CH₃)₂ oil 575 CH CF₃ 0 O CONHOCH₂CH₃ 114-116 576 CH CF₃ 0 O CONHCH₂CF₃ 74-76 577 CH CF₃ 0 O CON(CH₂CH₂Cl)₂ oil 578 CH CF₃ 0 O CONH-c-C₄H₇ oil 579 CH CF₃ 0 O CON(CH₂CH₂CH₃)CH₂-c-C₃H₅ oil 580 CH CF₃ 0 O CON(CH₃)-c-C₆H₁₁ oil 581 CH CF₃ 0 O CON(CH₂CH₃)CH₂C(═CH₂)CH₃ oil 582 CH CF₃ 0 O CONHOCH₂CH═CH₂ 90-92 583 CH CF₃ 0 O CONHOCH₂C₆H₅ 126-128 584 CH CF₃ 0 O CON(CH₃)CH₂COOCH₃ oil 585 CH CF₃ 0 O COONHCH₃ 230-232 586 CH CF₃ 0 O CONHCH₂CH₃ 83-85 587 CH CF₃ 0 O CONHCH(CH₃)COOCH₃ 104-106 588 CH CF₃ 0 O CONHCH(i-C₃H₇)COOCH₃ oil 589 CH CF₃ 0 O CON(CH₃)CH₂CON(CH₃)₂ oil 590 CH CF₃ 0 O CON(CH₃)-t-C₄H₉ oil 591 CH CF₃ 0 O CONHO-t-C₄H₉ 103-105 592 CH CF₃ 0 O CON(CH₃)CH(i-C₃H₇)COOCH₃ oil 593 CH CF₃ 0 O CH(OCH₂CH₃)₂ oil 594 CH CF₃ 0 O

oil 595 CH CF₃ 0 O

oil 596 CH CF₃ 0 O

oil 597 CH CF₃ 0 O

oil 598 CH CF₃ 0 O

oil 599 CH CF₃ 0 O CONHCH₂CONHCH₃ 101-103 600 CH CF₃ 0 O CON(CH₂)₇ oil 601 CH CF₃ 0 O CON(CH₂)₆ oil 602 CH CF₃ 0 O CON(CH₂CH₃)CH₂CH₂OCH₃ oil 603 CH CF₃ 0 O

oil 604 CH CF₃ 0 O

oil 605 CH CF₃ 0 O

oil 606 CH CF₃ 0 O CON(CH₂CH₃)CH₂CH₂CN oil 607 CH CF₃ 0 O

oil 608 CH CF₃ 0 O CON(CH₂CH₃)-n-C₄H₉ oil 609 CH CF₃ 0 O

179-181 610 CH CF₃ 0 O CONHCH(CH₃)CONHCH₃ 136-138 611 CH CF₃ 0 O COON(CH₂)₄ 64-66 612 CH CF₃ 0 O CONHCH₂CON(CH₃)₂ 107-109 613 CH CF₃ 0 O CON(CH₂COOCH₂CH₃)₂ oil 614 CH CF₃ 0 O

180-182 615 CH CF₃ 0 O

221-223 616 CH CF₃ 0 O

234-236 617 CH CF₃ 0 O

oil 618 CH CF₃ 0 O CON(CH₃)CH₂-6-Cl-3-pyridyl oil 619 CH CF₃ 0 O

105-107 620 CH CF₃ 0 O CONHCH(CH₃)CH(OCH₃)₂ oil 621 CH CF₃ 0 O CONHCH₂CH₂SCH₃ oil 622 CH CF₃ 0 O CONHCH(CH₃)CH₂OCH₃ 70-72 623 CH CF₃ 0 O CONHCH₂CH₂NHCOCH₃ 124-126 624 CH CF₃ 0 O CONH(CH₂)₃OCH₂CH₃ oil 625 CH CF₃ 0 O CON(CH₂CH₃)CH₂CH₂CH₃ oil 626 CH CF₃ 0 O CON(CH₂CH₃)CH₂OCH₃ oil 627 CH CF₃ 0 O CONHCH₂CH₂SCH₂CH₃ oil 628 CH CF₃ 0 O CONHCH₂CH₂OCH₂CH₃ 59-61 629 CH CF₃ 0 O

Oil 630 CH CF₃ 0 O

174-176 631 CH CF₃ 0 O CONHCH(CH₃)CH(OCH₃)₂ oil 632 CH CF₃ 0 O CONHCH₂CH₂SCH₃ oil 633 CH CF₃ 0 O CONHCH(CH₃)CH₂OCH₃ 70-72 634 CH CF₃ 0 O CONHCH₂CH₂NHCOCH₃ 124-126 635 CH CF₃ 0 O CONH(CH₂)₃OCH₂CH₃ oil 636 CH CF₃ 0 O CON(CH₂CH₃)CH2CH₂CH₃ oil 637 CH CF₃ 0 O CON(CH₂CH₃)CH₂OCH₃ oil 638 CH CF₃ 0 O CONHCH₂CH₂SCH₂CH₃ oil 639 CH CF₃ 0 O CONHCH(CH₃)CH₂COOCH₂CH₃ oil 640 CH CF₃ 0 O CONH-4-COOCH₃—C₆H₄ 189-191 641 CH CF₃ 0 O CONH-4-CONH₂—C₆H₄ 265-267 642 CH CF₃ 0 O CONHCH₂CH₂Br oil 643 CH CF₃ 0 O CONHCH₂CH═CHCH₂Cl oil 644 CH CF₃ 0 O CONH-4-CONHCH₃—C₆H₄ 219-221 645 CH CF₃ 0 O CONHCH₂CH₂CH₂Br oil 646 CH CF₃ 0 O CONHCH₂CH₂CH₂OCH₃ oil 647 CH CF₃ 0 O CONH-4-CH₂CH₃—C₆H₄ 97-99 648 CH CF₃ 0 O CONHCH₂CH₂OCH(CH₃)₂ oil 649 CH CF₃ 0 O CONHCH₂CH₂CH₂OCH₂CH₃ oil 650 CH CF₃ 0 O

oil 651 CH CF₃ 0 O

64-66 652 CH CF₃ 0 O

oil 653 CH CF₃ 0 O

oil 654 CH CF₃ 0 O CH₂CON(CH₃)CH₂CH₃ oil 655 CH CF₃ 0 O CH₂CON(CH₃)₂ 58-60 656 CH CF₃ 0 O CH₂CON(CH₂)₄ 101-103 657 CH CF₃ 0 O

oil 658 CH CF₃ 0 O

90-92 659 CH CF₃ 0 O CH₂CONHCH₂CH₃ 104-106 660 CH CF₃ 0 O CH₂CON(CH₃)CH₂CH₂CH oil 661 CH CF₃ 0 O CH₂CON(CH₃)CH₂CH₂CH₃ oil 662 CH CF₃ 0 O CH₂CON(CH₃)CH₂CH oil (—OCH₂CH₂O—) 663 CH CF₃ 0 O CH₂CONHCH₂CH₃ 104-106 664 CH CF₃ 0 O CH₂CON(CH₃)CH₂CH₂CH oil 665 CH CF₃ 0 O CH₂CON(CH₃)CH₂CH₂CH₃ oil 667 CH CF₃ 0 O CH₂CON(CH₃)CH₂CH oil (—OCH₂CH₂O—) 668 CH CF₃ 0 O

79-81 669 CH CF₃ 0 O CH₂CONHCH₂CH₂SCH₃ 65-67 670 CH CF₃ 0 O CH₂CONHCH(CH₃)CH₂OCH₃ 86-88 671 CH CF₃ 0 O CON(CH₃)CH₂CH₂OCO-c-C₄H₇ oil 672 CH CF₃ 0 O CH₂CONHCH₂CH₂Br 87-89 673 CH CF₃ 0 O CON(CH₃)CH₂CH₂OCOC₆H₅ oil 674 CH CF₃ 0 O CON(CH₃)CH₂CH₂OCO-c-C₃H₅ oil 675 CH CF₃ 0 O CONH-2-CH₃—C₆H₄ 104-106 676 CH CF₃ 0 O CH₂CON(i-C₃H₇)-4-F—C₆H₄ 102-104 677 CH CF₃ 0 O

oil 678 CH CF₃ 0 O

oil 679 CH CF₃ 0 O CON(CH₃)CH₂CH₂OCONHC₆H₅ 100-102 680 CH CF₃ 0 O CON(CH₃)CH₂CH₂OCONHCH₂ oil CH₃ 681 CH CF₃ 0 O CON(CH₃)CH₂CH₂OSO₂CH₃ oil 682 CH CF₃ 0 O CH₂CONH-c-C₄H₇ 133-135 683 CH CF₃ 0 O CH₂CONHCH₂CN 158-160

TABLE 2

No. X Y W R¹ m.p. [° C.] 684 N (CF₂)₃CHF₂ O CH₃ 685 N (CF₂)₂CF₃ O CH₂CH₃ 686 N (CF₂)₂CF₃ O COOCH₂CH₃ 687 N (CF₂)₂CF₃ O OH 688 N (CF₂)₂CF₃ O OCH₃ 689 N CF₂CF₃ O CH₃ 690 N CF₂CF₃ O CH₂CH₃ 691 N CF₂CF₃ S CH₃ 692 N CF2CF₃ S CH₂CH₃ 693 N CF₂CF₃ S (CH₂)₂CH₃ 694 CH CF₃ O CH₃ oil 695 CH CF₃ O CH₂CH₃ 696 CH CF₃ O (CH₂)₂CH₃ 697 CH CF₃ O CH(CH₃)₂ 698 CH CF₃ O (CH₂)₃CH₃ 699 CH CF₃ O CH(CH₃)CH₂CH₃ 700 CH CF₃ O CH₂CH(CH₃)₂ 701 CH CF₃ O C(CH₃)₃ oil 702 CH CF₃ O (CH₂)₄CH₃ 703 CH CF₃ O CH(CH₃)(CH₂)₂CH₃ 704 CH CF₃ O (CH₂)₂CH(CH₃)₂ 705 CH CF₃ O CH₂C(CH₃)₃ 706 CH CF₃ O Cyclo-C₅H₉ 707 CH CF₃ O Cyclo-C₆H₁₁ 708 CH CF₃ O CHO 709 CH CF₃ O CH═CH₂ 710 CH CF₃ O CH₂CH═C(CH₃)₂ 711 CH CF₃ O CH₂CH═CH₂ 712 CH CF₃ O C(CH₃)═CH₂ 713 CH CF₃ O (CH₂)₅C═CH₂ 714 CH CF₃ O C(═CHCH₃)CH₃ 715 CH CF₃ O CH₂C≡CH 716 CH CF₃ O CH₂CH₂C≡CH 717 CH CF₃ O CH₂C≡CCH₂CH₃ 718 CH CF₃ O (CH₂)₄C≡CH 719 CH CF₃ O CHFCF₃ 720 CH CF₃ O COOCH₂CH₃ 721 CH CF₃ O CH₂CH₂OH 722 CH CF₃ O CH₂CH₂OCH₃ 723 CH CF₃ O CH₂COOC(CH₃)₃ 724 CH CF₃ O CH₂SC₆H₅ 725 CH CF₃ O CH₂CONHCH₃ 726 CH CF₃ O CH₂CH(OH)CH₂CH 727 CH CF₃ O CH₂COCH₃ 728 CH CF₃ O COCH3 729 CH CF₃ O CH₂OC₆H₅ 730 CH CF₃ O COC₆H₅ 731 CH CF₃ O CF₂CH₃ 732 CH CF₃ O CH₂CN 733 CH CF₃ O CH₂CH(—O—)CH₂ 734 CH CF₃ O CH₂(4-OCH₃)C₆H₅ 735 CH CF₃ O CH₂CH(OH)CH₂SC₆H₅ 736 CH CF₃ O CH═CF₂ 737 CH CF₃ O CCl═CHCl 738 CH CF₃ O 2-Pyridyl 739 CH CF₃ O OC₆H₅ 740 CH CF₃ O OH 741 CH CF₃ O OCH₃ 742 CH CF₃ O OCH₂CH₃ 743 CH CF₃ O OCHF₂ 744 CH CF₃ O OCH₂C₆H₅ 745 CH CF₃ O SCH₃ 746 CH CF₃ O SC₆H₅ 747 CH CF₃ O NH₂ 748 CH CF₃ O NHCH₃ 749 CH CF₃ O NHCH₂CH₃ 750 CH CF₃ O N(CH₂CH₃)₂ 751 CH CF₃ O N(CH₂CN)₂ 752 CH CF₃ O N(CH₃)₂ 753 CH CF₃ O NHCOCH₃ 754 CH CF₃ O NHCOCH₂CH₃ 755 CH CF₃ O OSO₂CH₃ 756 CH CF₃ O SOCH₂(4-Br)—C₆H₄ 757 CH CF₃ O N(CH₃)COOCH₂C₆H₅ 758 N CF₃ O CH₃ 759 N CF₃ O CH₂CH₃ 760 N CF₃ O (CH₂)₂CH₃ 761 N CF₃ O CH(CH₃)₂ 762 N CF₃ O (CH₂)₃CH₃ 763 N CF₃ O CH₂CH(CH₃)₂ 764 N CF₃ O C(CH₃)₃ 765 N CF₃ O CH₂C(CH₃)₃ 766 N CF₃ O Cyclo-C₅H₉ 767 N CF₃ O Cyclo-C₆H₁₁ 768 N CF₃ O CH₂C═C(CH₃)₂ 769 N CF₃ O CH₂CH₂C═CH₂ 770 N CF₃ O CH₂CH═CH₂ 771 N CF₃ O (CH₂)₅CH═CH₂ 772 N CF₃ O CH₂C≡CH 773 N CF₃ O CH₂C≡CCH₂CH₃ 774 N CF₃ O CHFCF₃ 775 N CF₃ O COOCH₂CH₃ 776 N CF₃ O CH₂CH₂OH 777 N CF₃ O CH₂CH₂OCH₃ 778 N CF₃ O CH₂COOC(CH₃)₃ 779 N CF₃ O CH₂SC₆H₅ 780 N CF₃ O CH₂CONHCH₃ 781 N CF₃ O CH₂CH(OH)CH₂OH 782 N CF₃ O CHO 783 N CF₃ O COCH₃ 784 N CF₃ O CH₂OC₆H₅ 785 N CF₃ O COC₆H₅ 786 N CF₃ O CF₂CH₃ 787 N CF₃ O CH₂CN 788 N CF₃ O CH₂CH₂CN 789 N CF₃ O CH═CF₂ 790 N CF₃ O 2-Furyl 791 N CF₃ O OH 792 N CF₃ O OCH₃ 793 N CF₃ O OCH₂CH₃ 794 N CF₃ O OCHF₂ 795 N CF₃ O OCH₂C₆H₅ 796 N CF₃ O NH₂ 797 N CF₃ O NHCH₃ 798 N CF₃ O NHCH₂CH₃ 799 N CF₃ O N(CH₂CH₃)₂ 800 N CF₃ O N(CH₂CN)₂ 801 N CF₃ O N(CH₃)₂ 802 N CF₃ O NHCOCH₃ 803 N CF₃ O NHCOCH₂CH₃ 804 N CF₃ O OSO₂CH₃ 805 CH CF₃ S CH₃ 806 CH CF₃ S CH₂CH₃ 807 CH CF₃ S (CH₂)₂CH₃ 808 CH CF₃ S CHO 809 CH CF₃ S CHFCF₃ 810 CH CF₃ S CH₂C≡CH 811 CH CF₃ S COOCH₂CH₃ 812 CH CF₃ S CH₂COOC(CH₃)₃ 813 CH CF₃ S CH₂CN 814 N CF₃ S CH₃ 815 N CF₃ S CH₂CH₃ 816 N CF₃ S (CH₂)₂CH₃ 817 N CF₃ S CHFCF₃ 818 N CF₃ S CH₂CH₂OH 819 N CF₃ S CH₂COOC(CH₃)₃ 820 N CH₂CH₂Cl O CH₂CH₃ 821 N CH₂CH₂Cl O NH₂ 822 N CH₂Cl O CH₃ 823 CH CHF₂ O CH₃ 824 CH CHF₂ O CH₂CH₃ 825 CH CHF₂ O (CH₂)₂CH₃ 826 CH CHF₂ O CH₂C═CH₂ 827 CH CHF₂ O C(CH₃)═CH₂ 828 CH CHF₂ O COOCH₂CH₃ 829 CH CHF₂ O CH₂CONHCH₃ 830 CH CHF₂ O CF₂CH₃ 831 CH CHF₂ O CHO 832 CH CHF₂ O NH₂ 833 CH CHF₂ O NHCOCH₃ 834 N CHF₂ O CH₃ 835 N CHF₂ O CH₂CH₃ 836 N CHF₂ O CH(CH₃)(CH₂)₄CH₃ 837 N CHF₂ O CH₂CH═CH₂ 838 N CHF₂ O COOCH₂CH₃ 839 N CHF₂ O NH₂

TABLE 3

No. X Y m V R¹ m.p. [° C.] 840 N (CF₂)₃CHF₂ 0 O CH₃ 841 N (CF₂)₂CF₃ 0 O CH₂CH₃ 842 N (CF₂)₂CF₃ 0 O COOCH₂CH₃ 843 N (CF₂)₂CF₃ 0 O SH 844 N (CF₂)₂CF₃ 0 O SCH₃ 845 N (CF₂)₂CF₃ 0 O SCH₂C≡CH 846 N CF₂CF₃ 0 O CH₃ 847 N CF₂CF₃ 0 O CH₂CH₃ 848 N CF₃ 0 O CH₃ 849 N CF₃ 0 O CH₂CH₃ 850 N CF₃ 0 O (CH₂)₂CH₃ 851 N CF₃ 0 O CH(CH₃)₂ 852 N CF₃ 0 O (CH₂)₃CH₃ 853 N CF₃ 0 O CH₂CH(CH₃)₂ 854 N CF₃ 0 O C(CH₃)₃ 855 N CF₃ 0 O CH₂C(CH₃)₃ 856 N CF₃ 0 O Cyclo-C₅H₉ 857 N CF₃ 0 O Cyclo-C₆H₁₁ 858 N CF₃ 0 O CH₂CH═C(CH₃)₂ 859 N CF₃ 0 O CH₂CH₂CH═CH₂ 860 N CF₃ 0 O CH₂CH═CH₂ 861 N CF₃ 0 O (CH₂)₅CH═CH₂ 862 N CF₃ 0 O CH₂C≡CH 863 N CF₃ 0 O CH₂C≡CCH₂CH₃ 864 N CF₃ 0 O CHFCF₃ 865 N CF₃ 0 O COOCH₂CH₃ 866 N CF₃ 0 O CH₂CH₂OH 867 N CF₃ 0 O CH₂CH₂OCH₃ 868 N CF₃ 0 O CH₂COOC(CH₃)₃ 869 N CF₃ 0 O CH₂SPh 870 N CF₃ 0 O CH₂CONHCH₃ 871 N CF₃ 0 O CH₂CH(OH)CH₂O 872 N CF₃ 0 O CHO 873 N CF₃ 0 O COCH₃ 874 N CF₃ 0 O CH₂OC₆H₅ 875 N CF₃ 0 O COPh 876 N CF₃ 0 O CF₂CH₃ 877 N CF₃ 0 O CH₂CN 878 N CF₃ 0 O CH₂CH₂CN 879 N CF₃ 0 O CH═CF₂ 880 N CF₃ 0 O 2-Furyl 881 N CF₃ 0 O OH 882 N CF₃ 0 O OCH₃ 883 N CF₃ 0 O OCH₂CH₃ 884 N CF₃ 0 O OCHF₂ 885 N CF₃ 0 O OCH₂Ph 886 N CF₃ 0 O NH₂ 887 N CF₃ 0 O NHCH₃ 888 N CF₃ 0 O NHCH₂CH₃ 889 N CF₃ 0 O N(CH₂CH₃)₂ 890 N CF₃ 0 O N(CH₂CN)₂ 891 N CF₃ 0 O N(CH₃)₂ 892 N CF₃ 0 O NHCOCH₃ 893 N CF₃ 0 O NHCOCH₂CH₃ 894 N CF₃ 0 O OSO₂CH₃ 895 N CH₂CH₂Cl 0 O CH₂CH₃ 896 N CH₂CH₂Cl 0 O NH₂ 897 N CH₂Cl 0 O CH₃ 898 N CHF₂ 0 O CH₃ 899 N CHF₂ 0 O CH₂CH₃ 900 N CHF₂ 0 O CH(CH₃)(CH₂)₄CH₃ 901 N CHF₂ 0 O CH₂CH═CH₂ 902 N CHF₂ 0 O COOCH₂CH₃ 903 N CHF₂ 0 O NH₂ 904 CH CF₃ 0 O CH₃ 60-61 905 CH CF₃ 1 O CH₃ 906 CH CF₃ 0 O CH₂CH₃ oil 907 CH CF₃ 1 O CH₂CH₃ oil 908 CH CF₃ 0 O (CH₂)₂CH₃ oil 909 CH CF₃ 1 O (CH₂)₂CH₃ oil 910 CH CF₃ 0 O CH(CH₃)₂ 911 CH CF₃ 1 O CH(CH₃)₂ 912 CH CF₃ 0 O (CH₂)₃CH₃ 913 CH CF₃ 1 O (CH₂)₃CH₃ 914 CH CF₃ 0 O CH(CH₃)CH₂CH₃ 915 CH CF₃ 1 O CH(CH₃)CH₂CH₃ 916 CH CF₃ 0 O CH₂CH(CH₃)₂ 917 CH CF₃ 1 O CH₂CH(CH₃)₂ 918 CH CF₃ 0 O C(CH₃)₃ 919 CH CF₃ 1 O C(CH₃)₃ 920 CH CF₃ 0 O (CH₂)₄CH₃ 921 CH CF₃ 1 O (CH₂)₄CH₃ 922 CH CF₃ 0 O CH(CH₃)(CH₂₎ ₂CH₃ 923 CH CF₃ 0 O (CH₂)₂CH(CH₃)₂ 924 CH CF₃ 0 O CH₂C(CH₃)₃ 925 CH CF₃ 0 O cyclo-C₅H₉ 926 CH CF₃ 0 O cyclo-C₆H₁₁ 927 CH CF₃ 0 O CH₂(3-Thienyl) oil 928 CH CF₃ 0 O CHO 929 CH CF₃ 0 O CH═CH₂ 930 CH CF₃ 0 O CH₂Ph 61-63 931 CH CF₃ 0 O CH₂CH═C(CH₃)₂ 932 CH CF₃ 0 O CH₂CH═CH₂ 933 CH CF₃ 0 O C(CH₃)═CH₂ 934 CH CF₃ 0 O (CH₂)₅C═CH₂ 935 CH CF₃ 0 O C(═CHCH₃)CH₃ 936 CH CF₃ 0 O CH₂C≡CH 937 CH CF₃ 0 O CH₂CH₂C≡CH₂ 938 CH CF₃ 0 O CH₂C≡CCH₂CH₃ 939 CH CF₃ 0 O (CH₂)₄C≡CH 940 CH CF₃ 0 O CHFCF₃ 941 CH CF₃ 0 O COOCH₂CH₃ 942 CH CF₃ 0 O CH₂CH₂OH 943 CH CF₃ 0 O CH₂CH₂OCH₃ 944 CH CF₃ 0 O CH₂COOC(CH₃)₃ 945 CH CF₃ 0 O CH₂SPh 946 CH CF₃ 0 O CH₂CONHCH₃ 947 CH CF₃ 0 O CH₂CH(OH)CH₂OH 948 CH CF₃ 0 O CH₂COCH₃ 949 CH CF₃ 0 O COCH3 950 CH CF₃ 0 O CH₂Oph 951 CH CF₃ 0 O COPh 952 CH CF₃ 0 O CF₂CH₃ 953 CH CF₃ 0 O CH₂CN oil 954 CH CF₃ 0 O CH₂CH(—O—)CH₂ 955 CH CF₃ 0 O CH₂(4-OCH₃)Ph 956 CH CF₃ 0 O CH₂CH(OH)CH₂SPh 957 CH CF₃ 0 O CH═CF₂ 958 CH CF₃ 0 O CCl═CHCl 959 CH CF₃ 0 O Ph 120-121 960 CH CF₃ 0 O 2-Thienyl 87-89 961 CH CF₃ 0 O OPh 962 CH CF₃ 0 O OH 963 CH CF₃ 0 O OCH₃ 964 CH CF₃ 0 O OCH₂CH₃ 965 CH CF₃ 0 O OCHF₂ 966 CH CF₃ 0 O OCH₂Ph 967 CH CF₃ 0 O SCH₃ 968 CH CF₃ 0 O SPh 969 CH CF₃ 0 O NH₂ 190-191 970 CH CF₃ 0 O NHCH₃ 971 CH CF₃ 0 O NHCH₂CH₃ 972 CH CF₃ 0 O N(CH₂CH₃)₂ 973 CH CF₃ 0 O N(CH₂CN)₂ 974 CH CF₃ 0 O N(CH₃)₂ 975 CH CF₃ 0 O NHCOCH₃ 976 CH CF₃ 0 O NHCOCH₂CH₃ 977 CH CF₃ 0 O OSO₂CH₃ 978 CH CF₃ 0 O SOCH₂(4-Br)—C₆H₄ 979 CH CF₃ 0 O N(CH₃)COOCH₂Ph 980 CH CF₃ 0 NCH₃ CH₃ 981 CH CF₃ 0 NCH₂CH₃ CH₃ 982 CH CF₃ 0 NCH₂CH₃ CH₂CH₃ 983 CH CF₃ 0 NCH₂CN CH₂CH₃ 984 CH CF₃ 0 NCH₂OCH₃ NHCH₃ 985 CH CF₃ 0 NCH₂OCH₂CH₃ CN 986 CH CF₃ 0 NCH₂CH═CH₂ CH₃ 987 CH CF₃ 0 NCH₂CH═CF₂ SCH₃ 988 CH CF₃ 0 NCH₂OCH₃ SCH₂CH₃ 989 CH CF₃ 0 NCH₂OCH₃ SCH₂Ph 990 CH CHF₂ 0 O CH₃ 991 CH CHF₂ 0 O CH₂CH₃ 992 CH CHF₂ 0 O (CH₂)₂CH₃ 993 CH CHF₂ 0 O CH₂CH═CH₂ 994 CH CHF₂ 0 O C(CH₃)═CH₂ 995 CH CHF₂ 0 O COOCH₂CH₃ 996 CH CHF₂ 0 O CH₂CONHCH₃ 997 CH CHF₂ 0 O CF₂CH₃ 998 CH CHF₂ 0 O CHO 999 CH CHF₂ 0 O NH₂ 1000 CH CHF₂ 0 O NHCOCH₃ 1001 N CF₂CF₃ 0 S CH₃ 1002 N CF₂CF₃ 0 S CH₂CH₃ 1003 N CF₂CF₃ 0 S (CH₂)₂CH₃ 1004 N CF₃ 0 S CH₃ 1005 N CF₃ 0 S CH₂CH₃ 1006 N CF₃ 0 S (CH₂)₂CH₃ 1007 N CF₃ 0 S CHFCF₃ 1008 N CF₃ 0 S CH₂CH₂OH 1009 N CF₃ 0 S CH₂COOC(CH₃)₃ 1010 CH CF₃ 0 S CH₃ 1011 CH CF₃ 0 S CH₂CH₃ 1012 CH CF₃ 0 S (CH₂)₂CH₃ 1013 CH CF₃ 0 S CHO 1014 CH CF₃ 0 S CHFCF₃ 1015 CH CF₃ 0 S CH₂C≡CH 1016 CH CF₃ 0 S COOCH₂CH₃ 1017 CH CF₃ 0 S CH₂COOC(CH₃)₃ 1018 CH CF₃ 0 S CH₂CN

TABLE 4

No. X Y m V R² R³ m.p. 1019 N (CF₂)₃CHF₂ 0 S H CH₂CH₃ 1020 N CF₂CF₂CF₃ 0 S H CH₂CH₃ 1021 N CF₂CF₃ 0 S H CH₂CH₃ 1022 N CH₂CH₂Cl 0 S H CH₂CH₃ 1023 N CH₂Cl 0 S H CH₂CH₃ 1024 N CF₃ 0 S CH₂CH₃ CH₂CH₃ 1025 N CF₃ 0 S (CH₂)₂CH₃ H 1026 N CF₃ 0 S CH(CH₃)₂ H 1027 N CF₃ 0 S CH₂CH(CH₃)₂ H 1028 N CF₃ 0 S C(CH₃)₃ H 1029 CH CF₃ 0 S H CH₃ oil 1030 CH CF₃ 0 S H CH₂CH₃ oil 1031 CH CF₃ 0 S H C(CH₃)₃ oil 1032 CH CF₃ 0 S CH₂CH₃ COOCH₂CH₃ 1033 CH CF₃ 0 S (CH₂)₂CH₃ COOCH₂CH₃ 1034 CH CF₃ 0 S CH(CH₃)₂ COOCH₂CH₃ 1035 CH CF₃ 0 S CH(CH₃)₂ CONHCH₂CH₃ 1036 CH CF₃ 0 S CH(CH₃)₂ CONHCH₂CH₃ 1037 CH CF₃ 0 S CH(CH₃)₂ CON(CH₂CH₃)₂ 1038 CH CF₃ 0 S CH(CH₃)₂ CONH-cyclo-C₃H₇ 1039 CH CF₃ 0 S C(CH₃)₃ COOCH₂CH₃ 1040 CH CF₃ 0 S H CONHCH₂CH₃ 1041 CH CF₃ 0 S H CON(CH₂CH₃)₂ 1042 CH CF₃ 0 S H COOCH₂CH₃ oil 1043 CH CF₃ 0 S H CH₂COOCH₂CH₃ oil 1044 CH CF₃ 0 S H CH₂CHO 1045 CH CF₃ 0 S H CH₂OCH₃ 1046 CH CF₃ 0 S H CH₂OCH₂Ph 1047 CH CF₃ 0 S H H 1048 CH CF₃ 0 S Cyclo-C₅H₉ H 1049 CH CF₃ 0 S CON(CH₃)₂ CH₃ oil 1050 CH CF₃ 0 S CH₃ CH₂CH₂OH 1051 CH CF₃ 0 S CH₃ CH₂CH₂OCH₃ 1052 CH CF₃ 0 S CH₃ CH₂CH₂OCH₂Ph 1053 CH CF₃ 0 S CH₃ CH₂CH₂SPh 1054 CH CF₃ 0 S CH₃ CH₃ oil 1055 CH CF₃ 0 S CH₃ CH₂CH₂CHO 1055 CH CF₃ 0 S CH₃ CH₂CH₂CHNPh 1057 CH CF₃ 0 S CH₃ CH₂CH₂CONH₂ 1058 CH CF₃ 0 S H (4-CF₃O)C₆H₄ 120-121 1059 CH CF₃ 0 S CH₂C≡CH H 1060 CH CF₃ 0 S CH₂CH₂C≡CH H 1061 CH CF₃ 0 S CH₂C≡CCH₂CH₃ H 1062 CH CF₃ 0 S CH₂CH═C(CH₃)₂ H 1063 CH CF₃ 0 S CH₂CH₂CH═CH₂ H 1064 CH CF₃ 0 S CH₂CH═CH₂ H 1065 CH CF₃ 0 S C(CH₃)═CH₂ H 1066 CH CF₃ 0 S CHFCF₃ H 1067 CH CF₃ 0 S COOCH₂CH₃ H 1068 CH CF₃ 0 S CH₂CH₂OH H 1069 CH CF₃ 0 S CH₂CH₂OCH₃ H 1070 CH CF₃ 0 S CH₂COOC(CH₃)₃ H 1071 CH CF₃ 0 S CH₂COCH₃ H 1072 CH CF₃ 0 S COCH3 H 1073 CH CF₃ 0 S CH₂OPh H 1074 CH CF₃ 0 S COPh H 1075 CH CF₃ 0 S CO(4-Cl)—C₆H₄ H 1076 CH CF₃ 0 S CF₂CH₃ H 1077 CH CF₃ 0 S CH₂CN H 1078 CH CF₃ 0 S CH₂CH₂CN H 1079 N CF₃ 0 S H H 1080 N CF₃ 0 S H CH₂CH₂CN 1081 N CF₃ 0 S H CH₂CO₂C(CH₃)₃ 1082 N CF₃ 0 S H CH₂CHO 1083 N CF₃ 0 S H CH₂CH₂OH 1084 N CF₃ 0 S H CH₂CH₂OCH₃ 1085 N CF₃ 0 S Cyclo-C₅H₉ H 1086 N CF₃ 0 S CH₃ COOCH₂CH₃ 1087 N CF₃ 0 S CH₃ COOH 1088 N CF₃ 0 S CH₃ CONH₂ 1089 N CF₃ 0 S CH₃ CONHCH₂CH₃ 1090 N CF₃ 0 S CH₃ CON(CH₂CH₃)₂ 1091 N CF₃ 0 S CH₃ CONHCH₃ 1092 N CF₃ 0 S CH₃ CONHCH₂CN 1093 N CF₃ 0 S CH₃ CON(CH₂CN)₂ 1094 N CF₃ 0 S CH₃ CON(CH₃)₂ 1095 N CF₃ 0 S CH₂C≡CH OCH₂CH₃ 1096 N CF₃ 0 S CH₂CH₂C≡CH OCH₂CH₃ 1097 N CF₃ 0 S CH₂C≡CCH₂CH₃ OCH₂CH₃ 1098 N CF₃ 0 S CH₂CH═C(CH₃)₂ OCH₂CH₃ 1099 N CF₃ 0 S CH₂CH₂CH═CH₂ OCH₂CH₃ 1100 N CF₃ 0 S CH₂CH═CH₂ OCH₂CH₃ 1101 N CF₃ 0 S C(CH₃)═CH₂ OCH₂CH₃ 1102 N CF₃ 0 S CHFCF₃ OCH₂CH₃ 1103 N CF₃ 0 S COOCH₂CH₃ OCH₂CH₃ 1104 N CF₃ 0 S CH₂CH₂OH OCH₂CH₃ 1105 N CF₃ 0 S CH₂CH₂OCH₃ OCH₂CH₃ 1106 N CF₃ 0 S CH₂COOC(CH₃)₃ OCH₂CH₃ 1107 N CF₃ 0 S CH₂COCH₃ H 1108 N CF₃ 0 S COCH3 H 1109 N CF₃ 0 S CH₂Oph H 1110 N CF₃ 0 S COPh H 1111 N CF₃ 0 S CO(4-Cl)—C₆H₄ H 1112 N CF₃ 0 S CF₂CH₃ H 1113 N CF₃ 0 S CH₂CN H 1114 N CF₃ 0 S CH₂CH₂CN H 1115 CH CF₃ 0 O CH₂CH₃ CH₂CH₃ 1116 CH CF₃ 0 O (CH₂)₂CH₃ H 1117 CH CF₃ 0 O H CH₂CH₃ oil 1118 CH CF₃ 0 O CH(CH₃)₂ COOCH₂CH₃ 1119 CH CF₃ 0 O CH(CH₃)₂ COOH 1120 CH CF₃ 0 O CH(CH₃)₂ CONH₂ 1121 CH CF₃ 0 O CH(CH₃)₂ CH₃ 1122 CH CF₃ 0 O C(CH₃)₃ H 1123 CH CF₃ 0 O H CH₃ 1124 CH CF₃ 0 O H cyclo-C₅H₉ 1125 CH CF₃ 0 O H CH₂CH₂CH₃ 1126 CH CF₃ 0 O H Ph 103-10 1127 CH CF₃ 0 O H 2-Pyridyl 1128 CH CF₃ 0 O H 2-Furyl 1129 CH CF₃ 0 O Cyclo-C₅H₉ H 1130 CH CF₃ 0 O CH₃ COOCH₂CH₃ 1131 CH CF₃ 0 O CH₃ COOH 1132 CH CF₃ 0 O CH₃ CONH₂ 1133 CH CF₃ 0 O CH₃ CONHCH₂CH₃ 1134 CH CF₃ 0 O CH₃ CON(CH₂CH₃)₂ 1135 CH CF₃ 0 O CH₃ CONHCH₃ 1136 CH CF₃ 0 O CH₃ CONHCH₂CN 1137 CH CF₃ 0 O CH₃ CON(CH₂CN)₂ 1138 CH CF₃ 0 O CH₃ CON(CH₃)₂ 1139 CH CF₃ 0 O CH₂C≡CH H 1140 CH CF₃ 0 O CH₂CH₂C≡CH H 1141 CH CF₃ 0 O CH₂C≡CCH₂CH₃ H 1142 CH CF₃ 0 O CH₂CH═C(CH₃)₂ H 1143 CH CF₃ 0 O CH₂CH₂C═CH H 1144 CH CF₃ 0 O CH₂CH═CH₂ H 1145 CH CF₃ 0 O C(CH₃)═CH₂ H 1146 CH CF₃ 0 O CHFCF₃ H 1147 CH CF₃ 0 O COOCH₂CH₃ H 1148 CH CF₃ 0 O CH₂CH₂OH H 1149 CH CF₃ 0 O CH₂CH₂OCH₃ H 1150 CH CF₃ 0 O CH₂COOC(CH₃)₃ H 1151 CH CF₃ 0 O CH₂COCH₃ H 1152 CH CF₃ 0 O COCH3 H 1153 CH CF₃ 0 O CH₂Oph H 1154 CH CF₃ 0 O COPh H 1155 CH CF₃ 0 O CO(4-Cl)—C₆H₄ H 1156 CH CF₃ 0 O CF₂CH₃ H 1157 CH CF₃ 0 O CH₂CN H 1158 CH CF₃ 0 O CH₂CH₂CN H 1159 N CF₃ 0 O CH₂CH₃ CH₂CH₃ 1160 N CF₃ 0 O (CH₂)₂CH₃ H 1161 N CF₃ 0 O CH(CH₃)₂ CONH₂ 1162 N CF₃ 0 O CH(CH₃)₂ CH₃ 1163 N CF₃ 0 O C(CH₃)₃ H 1164 N CF₃ 0 O H CH₃ 1165 N CF₃ 0 O H CH₂CH₃ 1166 N CF₃ 0 O H CH₂CH₂CH₃ 1167 N CF₃ 0 O H Ph 1168 N CF₃ 0 O H 2-Pyridyl 1169 N CF₃ 0 O H 2-Furyl 1170 N CF₃ 0 O Cyclo-C₅H₉ H 1171 N CF₃ 0 O CH₃ COOCH₂CH₃ 1172 N CF₃ 0 O CH₃ COOH 1173 N CF₃ 0 O CH₃ CONH₂ 1174 N CF₃ 0 O CH₃ CONHCH₂CH₃ 1175 N CF₃ 0 O CH₃ CON(CH₂CH₃)₂ 1176 N CF₃ 0 O CH₃ CONHCH₃ 1177 N CF₃ 0 O CH₃ CONHCH₂CN 1178 N CF₃ 0 O CH₃ CON(CH₂CN)₂ 1179 N CF₃ 0 O CH₃ CON(CH₃)₂ 1180 N CF₃ 0 O CH₂C≡CH H 1181 N CF₃ 0 O CH₂CH₂C≡CH H 1182 N CF₃ 0 O CH₂C≡CCH₂CH₃ H 1183 N CF₃ 0 O CH₂CH═C(CH₃)₂ H 1184 N CF₃ 0 O CH₂CH₂CH═CH₂ H 1185 N CF₃ 0 O CH₂CH═CH₂ H 1186 N CF₃ 0 O C(CH₃)═CH₂ H 1187 N CF₃ 0 O CHFCF₃ H 1188 N CF₃ 0 O COOCH₂CH₃ H 1189 N CF₃ 0 O CH₂CH₂OH H 1190 N CF₃ 0 O CH₂CH₂OCH₃ H 1191 N CF₃ 0 O CH₂COOC(CH₃)₃ H 1192 N CF₃ 0 O CH₂COCH₃ H 1193 N CF₃ 0 O COCH3 H 1194 N CF₃ 0 O CH₂Oph H 1195 N CF₃ 0 O COPh H 1196 N CF₃ 0 O CO(4-Cl)—C₆H₄ H 1197 N CF₃ 0 O CF₂CH₃ H 1198 N CF₃ 0 O CH₂CN H 1199 N CF₃ 0 O CH₂CH₂CN H 1200 N CF₃ 0 O CH₂NHSO₂CH₃ CH₃ 1201 N CF₃ 0 O (CH₂)₂NHSO₂CH₃ CH₃ 1202 N CF₃ 0 O CH₂NHSO₂CH₂CH₃ CH₃ 1203 N CF₃ 0 O H CH₂NHSO₂CH₂Ph 1204 CH CF₃ 0 O (CH₂)₄NHSO₂CF₃ CH₃ 1205 CH CF₃ 0 O (CH₂)₂S(CH₂)₂CH₃ CH₂CH₂CH₃ 1206 CH CF₃ 0 O (CH₂)₄S(CH₂)₄OCH₃ CH₃ 1207 CH CF₃ 0 S CH₃ (CH₂)₂S(CH₂)₂CN 1208 CH CF₃ 0 S CH₂NHSO₂CH₂CH₃ CH₃ 1209 CH CF₃ 0 S CH₂NHSO₂CH₂Ph CH₂CH₂CH₃ 1210 CH CF₃ 0 S (CH₂₎ ₂NHSO₂CH₃ CF₃ 1211 CH CF₃ 0 S H CH₂NHSO₂CH₃ 1212 CH CF₃ 0 S CH(CH₃)CH₂NHPh CF₃ 1213 CH CF₃ 0 S (CH₂₎ ₂S(2-F)—C₆H₄ CH₂CH₂CH₃ 1214 CH CF₃ 0 S (CH₂)₆NHCH₂)₆OCH₃ CF₃ 1215 CH CF₃ 0 S H (CH₂)₂NH-(2-F)— C₆H₄ 1216 CH CF₃ 0 S (CH₂)₃NHCH₂CN H 1217 CH CF₃ 0 S (CH₂)₂O(3-Cl)—C₆H₄ CH₃ 1218 CH CF₃ 0 S CF₃ (CH₂)₆NHCH₂CF₃ 1219 CH CF₃ 0 S CH₃ (CH₂₎ ₂O(3-CH₃)—C₆H₄ 1220 CH CF₃ 0 O H CH₂NHPh 1221 CH CF₃ 0 O CH₃ (CH₂)₄S(2-Br)—C₆H₄ 1222 CH CF₃ 0 O (CH₂)₆NH(CH₂)₂OCH₃ CH₃ 1223 CH CF₃ 0 O (CH₂)₂NH(CH₂)₄OCH₃ H 1224 CH CF₃ 0 O CF₃ (CH₂₎ ₃NH-(4-CN)—C₆H₄ 1225 CH CF₃ 0 O (CH₂)₄NHCH₂CF₃ CH₃ 1226 CH CF₃ 0 O C₂F₅ (CH₂₎ ₂O(3-CH₃)—C₆H₄ 1227 CH CF₃ 0 O (CH₂)₄NHCH₂CN H 1228 CH CF₃ 0 O (CH₂₎ ₃O(4-Cl)—C₆H₄ C₂F₅

TABLE 5

No. X Y V R⁴ R⁵ R⁶ R⁷ m.p. [° C.] 1229 CH CF₃ O H H H H oil 1230 CH CF₃ O H H CH₃ H oil 1231 CH CF₃ O H H CH₂CH₃ H oil 1232 CH CF₃ O H H CH(CH₃)₂ H 1233 CH CF₃ O H H CH₂CH(CH₃)₂ H 1234 CH CF₃ O H H CH(CH₃)CH₂CH₃ H 1235 CH CF₃ O H H CH₂OH H 1236 CH CF₃ O H H CH(OH)CH₃ H 1237 CH CF₃ O H H CH₂SH H 1238 CH CF₃ O H H CH₂CH₂SCH₃ H 1239 CH CF₃ O H H (CH₂)₃NH₂ H 1240 CH CF₃ O H H (CH₂)₄NH₂ H 1241 CH CF₃ O H H CH═CH₂ H 1242 CH CF₃ O H H (CH₂)₂COOCH₃ H 1243 CH CF₃ O H H (CH₂)₂COOH H 1244 CH CF₃ O H H (CH₂)₂CONH₂ H 1245 CH CF₃ S CH₃ CH₃ H H 1246 CH CF₃ O H H CH₃ CH₃ oil 1247 CH CF₃ O H H CH₂COOCH₃ H 1248 CH CF₃ O H H CH₂COOH H 1249 CH CF₃ O H H CH₂CONH₂ H 1250 CH CF₃ O H H CH₂Ph H 1251 CH CF₃ O H H CH₂-(4-OH)—C₆H₄ H 1252 CH CF₃ O H H CH₂-(3-Indolyl) H 1253 CH CF₃ O CH₃ CH₃ H H oil 1254 CH CF₃ O CH₃ H H H oil 1255 CH CF₃ O CH₃ H H Ph 1256 CH CF₃ O H (CH₂)₄ H 1257 CH CF₃ NH H (CH₂)₄ H 1258 CH CF₃ NCH₃ H (CH₂)₄ H 1259 CH CF₃ NCH₂C₆H₄ H (CH₂)₄ H 1260 CH CF₃ NCH(CH₃)₂ H (CH₂)₄ H 1261 CH CF₃ O Ph H Ph H 1262 CH CF₃ NH Ph H Ph H 1263 CH CF₃ NCH₃ Ph H Ph H 1264 CH CF₃ NCH₂C₆H₄ Ph H Ph H 1265 N CF₃ O H H CH₂CH₃ H oil 1266 N CF₃ O H H CH(CH₃)₂ H 1267 N CF₃ O H H CH₂CH(CH₃)₂ H 1268 N CF₃ O H H CH₂COOH H 1269 N CF₃ O H H CH₂COOCH₃ H 1270 N CF₃ O H H CH₂CONH₂ H 1271 N CF₃ O CH₃ CH₃ H H 1272 N CF₃ O H (CH H 1273 N CF₃ O H H CH₂CH₂SCH₃ H 1274 CH CF₃ S H H H H oil

TABLE 6

No. X Y R⁸ R¹ m.p. [° C.] 1275 CH CF₃ CH₃ SH 209-210 1276 CH CF₃ CH₃ SCH₃ 1277 CH CF₃ CH₃ SCH₂CH₃ 1278 CH CF₃ CH₃ S(CH₂)₂CH₃ 1279 CH CF₃ CH₃ SCH(CH₃)₂ 1280 CH CF₃ CH₃ SPh 1281 CH CF₃ CH₃ S(CH₂)₃CH₃ 1282 CH CF₃ CH₃ SCH(CH₃)CH₂CH₃ 1283 CH CF₃ CH₃ SCH₂CH(CH₃)₂ 1284 CH CF₃ CH₃ OH 119-120 1285 CH CF₃ CH₃ OCH₃ 1286 CH CF₃ CH₃ OCH₂CH₃ 1287 CH CF₃ CH₃ OCHF₂ 1288 CH CF₃ CH₃ OCH₂Ph 1289 CH CF₃ CH₃ OCONHPh 1290 CH CF₃ CH₃ OCONH-(4-F)—C₆H₄ 1291 CH CF₃ CH₃ OCONH-(3,5-di-Cl)—C₆H₃ 1292 CH CF₃ CH₂CN OCH₃ 1293 CH CF₃ CH₂CN OCH₂CH₃ 1294 CH CF₃ CH₂CN OCHF₂ 1295 CH CF₃ CH₂CN OCH₂Ph 1296 CH CF₃ CH₂CN OCONHPh 1297 CH CF₃ CH₂CN OCONH-(4-F)—C₆H₄ 1298 CH CF₃ CH₂OCH₂CH₃ OCH₃ 1299 CH CF₃ CH₂OCH₂CH₃ OCH₂CH₃ 1300 CH CF₃ CH₂OCH₂CH₃ OCHF₂ 1301 CH CF₃ CH₂OCH₂CH₃ OCH₂Ph 1302 CH CF₃ CH₂OCH₂CH₃ OCONHPh 1303 CH CF₃ H CH₃ 203-204 1304 CH CF₃ H CH₂CH₃ 134-135 1305 CH CF₃ H (CH₂)₂CH₃ 1306 CH CF₃ H CH(CH₃)₂ 1307 CH CF₃ H Cyclo-C₃H₅ 1308 CH CF₃ H (CH₂)₃CH₃ 1309 CH CF₃ H CH(CH₃)CH₂CH₃ 1310 CH CF₃ H CH₂CH(CH₃)₂ 1311 CH CF₃ H CH═CH₂ 1312 CH CF₃ H CH₂CH═C(CH₃)₂ 1313 CH CF₃ H CH₂CH₂CH═CH₂ 1314 CH CF₃ H CH₂CH═CH₂ 1315 CH CF₃ H C(CH₃)═CH₂ 1316 CH CF₃ H CHFCF₃ 1317 CH CF₃ H COOCH₂CH₃ 1318 CH CF₃ H CH₂CH₂OH 1319 CH CF₃ H CH₂CH₂OCH₃ 1320 CH CF₃ H CH₂COOC(CH₃)₃ 1321 CH CF₃ CH₃ CH₂COOC(CH₃)₃ 1322 CH CF₃ CH₂CN CH₂COOC(CH₃)₃ 1323 CH CF₃ CH₂OCH₂CH₃ CH₂COOC(CH₃)₃ 1324 CH CF₃ H CH₂SPh 1325 CH CF₃ H CH₂CONHCH₃ 1326 CH CF₃ H CH₂COCH₃ 1327 CH CF₃ H COCH3 1328 CH CF₃ H CH₂Oph 1329 CH CF₃ H COPh 1330 CH CF₃ H CO(3-Cl)—C₆H₄ 1331 CH CF₃ H CF₂CH₃ 1332 CH CF₃ H CH₂CN 1333 CH CF₃ H CH₂CH₂CN 1334 CH CF₃ H CH₂CH(—O—)CH₂ 1336 CH CF₃ H CH₂(4-OCH₃)Ph 1337 N CF₃ CH₃ SH 1338 N CF₃ CH₃ SCH₃ 1339 N CF₃ CH₃ SCH₂CH₃ 1340 N CF₃ CH₃ SPh 1341 N CF₃ CH₃ SCH₂CH(CH₃)₂ 1342 N CF₃ CH₃ OH 1343 N CF₃ CH₃ OCH₃ 1344 N CF₃ CH₃ OCH₂CH₃ 1345 N CF₃ CH₃ OCH₂Ph 1346 N CF₃ CH₃ OCONHPh 1347 N CF₃ CH₂CN OCH₃ 1348 N CF₃ CH₂CN OCH₂CH₃ 1349 N CF₃ CH₂CN OCH₂Ph 1350 N CF₃ CH₂CN OCONHPh 1351 N CF₃ CH₂OCH₂CH₃ OCH₃ 1352 N CF₃ CH₂OCH₂CH₃ OCH₂Ph 1353 N CF₃ CH₂OCH₂CH₃ OCONHPh 1354 N CF₃ H CH₃ 1355 N CF₃ H CH₂CH₃ 1356 N CF₃ H (CH₂)₂CH₃ 1357 N CF₃ H CH(CH₃)₂ 1358 N CF₃ H (CH₂)₃CH₃ 1359 N CF₃ H CH(CH₃)CH₂CH₃ 1360 N CF₃ H CH₂CH(CH₃)₂ 1361 N CF₃ H CH₂C═C(CH₃)₂ 1362 N CF₃ H CH₂CH═CH₂ 1363 N CF₃ H C(CH₃)H═CH₂ 1364 N CF₃ H COOCH₂CH₃ 1365 N CF₃ H CH₂CH₂OH 1366 N CF₃ H CH₂CH₂OCH₃ 1367 N CF₃ H CH₂COOC(CH₃)₃ 1368 N CF₃ H CH₂SPh 1369 N CF₃ H CH₂CONHCH₃ 1370 N CF₃ H CH₂COCH₃ 1371 N CF₃ H COCH3 1372 N CF₃ H CH₂Oph 1373 N CF₃ H COPh 1374 N CF₃ H CH₂CN 1375 N CF₃ H CH₂CH₂CN 1376 CH CF₃ CH₃ CH₂CH₃ oil

C. Biological examples

Example 1

A Petri dish whose bottom is covered with filter paper and which contains about 5 ml of culture medium is prepared. Pieces of filter paper with about 30, 24-hour-old eggs of the American tobacco budworm (Heliothis virescens) are dipped into an aqueous solution of the formulated preparation to be examined for 5 seconds and subsequently placed in the Petri dish. A further 200 μl of the aqueous solution are spread over the culture medium. The Petri dish is closed and then kept at about 25° C. in a climatized chamber. After 6 days' storage, the effect of the preparation on the eggs and the larvae which may have hatched from these is determined. At a concentration of 300 ppm (based on the content of active compound), the preparations of Example Nos. 79 and 88 effect a mortality of 90-100%.

Example 2

Germinated broad bean seeds (Vicia faba) with radicles are transferred into brown glass bottles filled with tap water and subsequently populated with approximately 100 black bean aphids (Aphis fabae) belegt. Plants and aphids are then dipped for 5 seconds into an aqueous solution of the formulated preparation to be examined. After the solution has dripped off, plant and animals are kept in a climatized chamber (16 hours of light/day, 25° C., 40-60% relative atmospheric humidity. After 3 and 6 days' storage, the effect of the preparation on the aphids is determined. At a concentration of 300 ppm (based on the content of active compound), the preparations of Example Nos. 79, 78, 80, 81, 83, 84, 88, 133, 135, 136, 137, 138, 139, 1117, 1229, 1230, 1231, 1246 and 1254 effect a mortality of 90-100% among the aphids.

Example 3

The leaves of 12 rice plants having a stem length of 8 cm are dipped for 5 seconds into an aqueous solution of the formulated preparation to be examined. After the solution has dripped off, the rice plants treated in this manner are placed in a Petri dish and populated with approximately 20 larvae (L3 stage) of the rice leaf hopper species Nilaparvata lugens. The Petri dish is closed and stored in a climatized chamber (16 hours of light/day, 25° C., 4060% relative atmospheric humidity). After 6 days' storage, the mortality among the leaf hopper larvae is determined. At a concentration of 300 ppm (based on the content of active compound), the preparations of Example Nos. 88 139 and 927 effect a mortality of 90-100%.

Example 4

Germinated broad bean seeds (Vicia faba) with radicles are transferred into brown glass bottles filled with tap water. Four milliliters of an aqueous solution of the formulated preparation to be examined are pipetted into the brown glass bottle. The broad bean is subsequently heavily populated with approximately 100 black bean aphids (Aphis fabae). Plant and animals are then stored in a climatized chamber (16 hours of light/day, 25° C., 40-60% relative atmospheric humidity). After 3 and 6 days' storage, the root-systemic activity of the preparation on the aphids is determined. At a concentration of of 30 ppm (based on the content of active compound), the Preparations of Example Nos. 78, 79, 80, 81, 83, 84, 88,133, 135, 136, 137, 138, 139,187, 1117, 1229,1230, 1231,1246 and 1254 effect a mortality of 90-100% among the aphids by root-systemic action. 

What is claimed is:
 1. A 4-haloalkyl-3-heterocyclylpyridine or 4-haloalkyl-5-heterocyclyl-pyrimidine of the formula I if desired in the form of its salt

wherein Y is halo-C₁-C₆alkyl; x is CH or N; m is 0 or1; Q is a 5-membered heterocyclic group

in which a) X¹ = W, X² = NR^(a), X³ = CR^(b)R¹ or b) X¹ = NR^(a), X² = CR^(b)R¹, X³ = W or c) X¹ = V, X² = CR^(a)R¹, X³ = NR^(b) or d) X¹ = V, X² = CR^(a)R², X³ = CR^(b)R³ or e) X¹ = V, X² = CR⁴R⁵, X³ = CR⁶R⁷ or f) X¹ = NR^(a), X² = CR^(b)R¹, X³ = NR⁸;

R^(a) and R^(b) together are a bond V is oxygen, sulfur or NR⁹; W is oxygen or sulfur; R¹ is hydrogen, (C₁-C₂₀)-alkyl, (C₂-C₂₀)-alkenyl, (C₂-C₂₀)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₆-C₈)-cycloalkynyl, where the six last-mentioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, nitro, hydroxyl, —C(═W)R¹⁰, —C(═NOR¹⁰)R¹⁰, —C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OC(═W)OR¹⁰, —NR¹⁰C(═W)R¹⁰, —N[C(═W)R¹⁰]₂, —NR¹⁰C(═W)OR¹⁰, —C(═W)NR¹⁰—NR¹⁰ ₂, —C(═W)NR¹⁰—NR¹⁰[C(═W)R¹⁰], —NR¹⁰—C(═W)NR¹⁰ ₂, —NR¹⁰—NR¹⁰C(═W)R¹⁰, —NR¹⁰—N[C(═W)R¹⁰]₂, —N[(C═W)R¹⁰], —NR¹⁰ ₂, —NR¹⁰—NR¹⁰[(C═W)R¹⁰]₂, —NR¹⁰—NR¹⁰[(C═W)WR¹⁰], —NR¹⁰—R¹⁰[(C═W)NR¹⁰]₂, —NR¹⁰(C═NR¹⁰)R¹⁰, —NR¹⁰(C═NR¹⁰)NR¹⁰ ₂ —O—NR¹⁰ ₂, —O—NR¹⁰(C═W)R¹⁰, —SO₂NR¹⁰ ₂, —NR¹⁰S¹⁰ ₂R¹⁰, —SO₂OR¹⁰, —OSO₂R¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SiR¹⁰ ₃, —SeR¹⁰, —PR¹⁰ ₂, —P(═W)R¹⁰ ₂, —SOR¹⁰, —SO₂R¹⁰, —PW₂R¹⁰ ₂, —PW₃R¹⁰ ₂, aryl and heterocyclyl, the two last-mentioned radicals optionally being substituted by one or more radicals from the group (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₆-C₈)cycloalkynyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl, halogen, —OR¹⁰, —NR¹⁰ ₂—SR¹⁰, —SiR¹⁰ ₃, —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —SOR¹⁰, —SO₂R¹⁰, nitro, cyano and hydroxyl; aryl, which is optionally substituted by one or more radicals from the group (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl and (C₆C₈)-cycloalkynyl, where these six abovementioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, nitro, —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰ and —SO₂R¹⁰; halogen, cyano, nitro, —C(═W)R¹⁰, —C(═W)OR¹⁰)R¹⁰, —C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OC(═W)OR¹⁰, —NR¹⁰C(═W)R¹⁰, —N[C(═W)R¹⁰]₂, —NR¹⁰C(═W)OR¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SiR¹⁰ ₃, —PR¹⁰ ₂, —SOR¹⁰, —SO₂R¹⁰, —PW₂R¹⁰ ₂ and —PW₃R¹⁰ ₂, heterocyclyl, which is optionally substituted by one or more radicals from the group (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl and (C₆-C₈)-cycloalkynyl, where the six abovementioned radicals are optionally substituted by one or more radicals from the group cyano, nitro, halogen, —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —NR¹⁰C(═W)R¹⁰, —N[C(═W)R¹⁰]₂, —OC(═W)R¹⁰, —OC(═W)OR¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰ and —SO₂R¹⁰; halogen, cyano, nitro, —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰ and —SO₂R¹⁰, —OR¹⁰, —NR¹⁰, —SR¹⁰, —SOR¹⁰, —SO₂R¹⁰, —C(═W)R¹⁰, —C(═NOR¹⁰)R¹⁰, —C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OC(═W)OR¹⁰, —NR¹⁰C(═W)R¹⁰, —N[C(═W)R¹⁰]₂, —NR¹⁰C(═W)OR¹⁰, —C(═W)NR¹⁰—NR¹⁰ ₂, —C(═W)NR¹⁰—NR¹⁰C(═W)R¹⁰, —NR¹⁰—C(═W)NR¹⁰ ₂, —NR¹⁰—NR¹⁰C(═W)R¹⁰, —NR¹⁰—NC(═W)R¹⁰ ₂, —N(C═W)R¹⁰—NR¹⁰ ₂, —NR¹⁰-NR¹⁰[(C═W)R¹⁰], —NR¹⁰—NR¹⁰[(C═W)WR^(10o), —NR¹⁰—NR¹⁰[(C═W)NR¹⁰ ₂], —NR¹⁰(C═NR¹⁰)R¹⁰, —NR¹⁰(C═NR¹⁰)NR¹⁰ ₂, —O—NR¹⁰ ₂, —O—NR¹⁰(C═W)R¹⁰, —SO₂NR¹⁰ ₂, —NR¹⁰SO₂R¹⁰, —SO₂R¹⁰, —OSO₂R¹⁰, —SC(═W)R¹⁰, —SC(═W)OR¹⁰, —SC(═W)R¹⁰, —PR¹⁰ ₂, —PW₂R¹⁰ ₂, —PW₃R¹⁰ ₂, SiR¹⁰ ₃ or halogen; R² and R³ independently of one another have the definitions given in R¹; R² and R³ together form a 5- to 7-membered ring which may be partially or fully unsaturated and may be interrupted by one or more atoms from the group nitrogen, oxygen and sulfur, the oxygen atoms not being directly adjacent to one another, and the ring optionally being substituted by one or more, but at most 5, radicals R¹; R⁴ and R⁶ independently of one another have the definitions given in R¹; R⁴ and R⁶ together form a 4- to 7-membered ring which may be partially or fully unsaturated and may be interrupted by one or more atoms from the group nitrogen, oxygen and sulfur, the oxygen atoms not being directly adjacent to one another, and the ring optionally being substituted by one or more, but at most 5, radicals R¹; R⁵ and R⁷ independently of one another are hydrogen, (C₁-C₂₀)-alkyl, (C₂₋C₂₀)-alkenyl, (C₂-C₂₀)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₆-C₈)-cycloalkynyl, where the six last-mentioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, nitro, hydroxyl, —C(═W)R¹⁰, —C(═NOR¹⁰)R¹⁰, —C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰]₂, —OC(═W)R¹⁰, —OC(═W)OR¹⁰, —NR¹⁰C(═W)R¹⁰, —N[C(═W)R¹⁰]₂, —NR¹⁰C(═W)OR¹⁰, —C(═W)NR¹⁰-NR¹⁰ ₂, —C(═W)NR¹⁰—NR¹⁰[C(═W)R¹⁰], —NR¹⁰—C(═W)NR¹⁰, —NR¹⁰—NR¹⁰C(═W)R¹⁰, —NR¹⁰—N[C(═W)R¹⁰]₂, —N[(C═W)R¹⁰]-NR¹⁰ ₂, —NR¹⁰-NR¹⁰[(C═W)R¹⁰], —NR¹⁰—NR¹⁰[(C═W)NR¹⁰], —NR¹⁰O—NR¹⁰[(C═W)NR¹⁰]₂, —N R¹⁰(C═N R¹⁰)R¹⁰, —NR¹⁰(C═NR¹⁰)NR¹⁰ ₂, —O—NR¹⁰ ₂, —O—NR¹⁰(C═W)R¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SiR¹⁰ ₃, —SeR¹⁰, —PR¹⁰ ₂, —P(═W)R¹⁰ ₂, —SOR¹⁰, —SO₂R¹⁰, —PW₂R¹⁰ ₂, —PW₃R¹⁰ ₂, aryl and heterocyclyl, of which the two mentioned last are optionally substituted by one or more radicals from the group (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₄-C₈)-cycloalkynyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl, halogen, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SiR¹⁰ ₃, —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —SOR¹⁰, —SO₂R¹⁰, nitro, cyano and hydroxyl; aryl, which is optionally substituted by one or more radicals from the group (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl and (C₆-C₈)-cycloalkynyl, where these six abovementioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, nitro, —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰ and —SO₂R¹⁰, halogen, cyano, nitro, —C(═W)R¹⁰, —C(═NOR¹⁰)R¹⁰, —C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OC(═W)OR¹⁰, —NR¹⁰C(═W)R¹⁰, —N[C(═W)R¹⁰]₂, —NR¹⁰C(═W)OR¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SiR¹⁰ ₃, —PR¹⁰ ₂, —SORR¹⁰, —SO₂R¹⁰, —PW₂R¹⁰ ₂ and —PW₃R¹⁰ ₂; pyridyl, which is optionally substituted by one or more radicals from the group (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl and (C₆-C₈)-cycloalkynyl, where the six abovementioned radicals are optionally substituted by one or more radicals from the group cyano, nitro, halogen, —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰ and —SO₂R¹⁰; halogen, cyano, nitro, —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰ and —SO₂R¹⁰, —C(═W)R¹⁰, —C(═NOR¹⁰)R¹⁰, —C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂ or halogen; R⁴ and R⁵ together form a 4- to 7-membered ring which may be partially unsaturated and may be interrupted by one or more atoms from the group nitrogen, oxygen and sulfur, oxygen atoms not being directly adjacent to one another, and the ring optionally being substituted by one or more, but at most 5, radicals R¹⁰; R⁴ and R⁵ together form one of the groups ═O, ═S or ═N—R⁹; R⁶ and R⁷ together form a 5- to 7-membered ring which may be partially unsaturated and may be interrupted by one or more atoms from the group nitrogen, oxygen and sulfur, oxygen atoms not being directly adjacent to one another, and the ring optionally being substituted by one or more, but at most 5, radicals R¹; R⁶ and R⁷ together form one of the groups ═O, ═S or ═N—R⁹; R⁸ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, (C₂-C₆)-alkenyl-C₃-C₈)-cycloalkyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl-C₄-C₈)-cycloalkenyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenyl, where the fourteen last-mentioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkyloxy, (C₂-C₆)-haloalkenyloxy, (C₂-C₆)-haloalkynyloxy, (C₃-C₈)-cycloalkoxy, (C₄-C₈)-cycloalkenyloxy, (C₃-C₈)-halocycloalkoxy, (C₄-C₈)-halocycloalkenyloxy, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkoxy, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkoxy, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenyloxy, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyloxy, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkoxy, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkoxy, (C₂-C₄)-alkynyl-(C₃-C₈)-cycloalkoxy, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenyloxy, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenyloxy, (C₁-C₄)-alkoxy-(C₁-C₆)-alkoxy, (C₁-C₄)-alkoxy-(C₂-C₆)-alkenyloxy, carbamoyl, (C₁-C₆)-mono- or dialkylcarbamoyl, (C₁-C₆)-mono- or dihaloalkylcarbamoyl, (C₃-C₈)-mono- or dicycloalkylcarbamoyl, (C₁-C₆)-alkoxycarbonyl, (C₃-C₈)-cycloalkoxycarbonyl, (C₁-C₆)-alkanoyloxy, (C₃-C₈)-cycloalkanoyloxy, (C₁-C₆)-haloalkoxycarbonyl, (C₁-C₆)-haloalkanoyloxy, (C₁-C₆)-alkaneamido, (C₁-C₆)-haloalkaneamido, (C₂-C₆)-alkeneamido, (C₃-C₈)-cycloalkaneamido, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkaneamido, (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio, (C₁-C₆)-haloalkylthio, (C₂-C₆)-haloalkenylthio, (C₂-C₆)-haloalkynylthio, (C₃-C₈)-cycloalkylthio, (C₄-C₈)-cycloalkenylthio, (C₃-C₈)-halocycloalkylthio, (C₄-C₈)-halocycloalkenylthio, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylthio, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylthio, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylthio, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylthio, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylthio, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylthio, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylthio, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylthio, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylthio, (C₁-C₆)-alkylsulfinyl, (C₂-C₆)-alkenylsulfinyl, (C₂-C₆)-alkynylsulfinyl, (C₁-C₆)-haloalkylsulfinyl, (C₂-C₆)-haloalkenylsulfinyl, (C₂-C₆)-haloalkynylsulfinyl, (C₃-C₈)-cycloalkylsulfinyl, (C₄-C₈)-cycloalkenylsulfinyl, (C₃-C₈)-halocycloalksulfinyl, (C₄-C₈)-halocycloalkenylsulfinyl, (C₃-C₈)-cycloalkyl-C₁-C₄)-alkylsulfinyl, (C₄-C₈)-cyloalkenyl-(C₁-C₄)-alkylsulfinyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylsulfinyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyIsulfinyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylsulfinyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylsulfinyl, (C₂-C₆)-alkynyl-C₃-C₈)-cycloalkylsulfinyI, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenyIsulfinyl, (C₂-CB)-alkenyl-(C₄-C₈)-cycloalkenylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₂-C₆)-alkenylsulfonyl, (C₂-C₆)-alkynylsulfonyl, (C₁-C₆)-haloalkylsulfonyl, (C₂-C₆)-haloalkenylsulfonyl, (C₂-C₆)-haloalkynylsulfonyl, (C₃-C₈)-cycloalkylsulfonyl, (C₄-C₈)-cycloalkenylsulfonyl, (C₃-C₈)-halocycloalkylsulfonyl, (C₄-C₈)-halocycloalkenylsulfonyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylsulfonyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkyl sulfonyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylsulfonyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylsulfonyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylsulfonyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycoalkylsulfonyl, (C₂-C₈)-cycloalkenyl-(C₃-C₈)-cycloalkylsulfonyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylsulfonyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylsulfonyl, (C₁-C₆,)-alkylamino, (C₂-C₆)-alkenylamino, (C₂-C₆)-alkynylamino, (C₁-C₆)-haloalkylamino, (C₂-C₆)-haloalkenylamino, (C₂-C₆)-haloalkynylamino, (C₃-C₈)-cycloalkylamino, (C₄-C₈)-cycloalkenylamino, (C₃-C₈)-halocycloalkamino, (C₄-C₈)-halocycloalkenylamino, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylamino, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylamino, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylamino, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylamino, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylamino, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylamino, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylamino, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylamino, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylamino, (C₁-C₆)-trialkylsilyl, aryl, aryloxy, arylthio, arylamino, arylcarbamoyl, aroyl, aroyloxy, aryloxycarbonyl, aryl-(C₁-C₄)-alkoxy, aryl-(C₂-C₄)-alkenyloxy, aryl-(C₁-C₄)-alkylthio, aryl-(C₂-C₄)-alkenylthio, aryl-(C₁-C₄)-alkylamino, aryl-(C₂-C₄)-alkenylamino, aryl-(C₁-C₆)-dialkylsilyl, diaryl-(C₁-C₆)-alkylsilyl, triarylsilyl and 5- or 6-membered heterocyclyl; of which the nineteen last-mentioned radicals are optionally substituted in their cyclic moiety by one or more substituents from the group halogen, cyano, nitro, amino, hydroxyl, thio, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-haloalkylthio, (C₁-C₄)-alkylamino, (C₁-C₄)-haloalkylamino, formyl and (C₁-C₄)-alkanoyl; aryl, which is optionally substituted by one or more radicals from the group halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkyloxy, (C₂-C₆)-haloalkenyloxy, (C₂-C₆)-haloalkynyloxy, (C₃-C₈)-cycloalkoxy, (C₄-C₈)-cycloalkenyloxy, (C₃-C₈)-halocycloalkoxy, (C₄-C₈)-halocycloalkenyloxy, carbamoyl, (C₁-C₆)-mono- or dialkylcarbamoyl, (C₁-C₆)-alkoxycarbonyl, (Ci-C₆)-alkanoyloxy, (C₁-C₆)-mono- or dihaloalkylcarbamoyl, (C₁-C₆)-haloalkoxycarbonyl, (C₁-C₆)-haloalkanoyloxy, (C₁-C₆)-alkaneamido, (C₁-C₆)-haloalkaneamido, (C₂-C₆)-alkeneamido, (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio, (C₁-C₆)-haloalkylthio, (C₂-C₆)-haloalkenylthio, (C₂-C₆)-haloalkynylthio, (C₃-C₈)-cycloalkylthio, (C₄-C₈)-cycloalkenylthio, (C₃-C₈)-halocycloalkthio, (C₃-C₈)-halocycloalkenylthio, (C₁-C₆)-alkylsulfinyl, (C₂-C₆)-alkenylsulfinyl, (C₂-C₆)-alkynylsulfinyl, (C₁-C₆)-haloalkylsulfinyl, (C₂-C₆)-haloalkenylsulfinyl, (C₂-C₆)-haloalkynylsulfinyl, (C₃-C₈)-cycloalkylsulfinyl, (C₄-C₈)-cycloalkenylsulfinyl, (C₃-C₈)-halocycloalksulfinyl, (C₄-C₈)-halocycloalkenylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₂-C₆)-alkenylsulfonyl, (C₂-C₆)-alkynylsulfonyl, (C₁-C₆)-haloalkylsulfonyl, (C₂-C₆)-haloalkenylsulfonyl, (C₂-C₆)-haloalkynylsulfonyl, (C₃-C₈)-cycloalkylsulfonyl, (C₄-C₈)-cycloalkenylsulfonyl, (C₃-C₈)-halocycloalksulfonyl, (C₄-C₈)-halocycloalkenylsulfonyl, (C₁-C₆)-alkylamino, (C₂-C₆)-alkenylamino, (C₂-C₆)-alkynylamino, (C₁-C₆)-haloalkylamino, (C₂-C₆)-haloalkenylamino, (C₂-C₆)-haloalkynylamino, (C₃-C₈)-cycloalkylamino, (C₄-C₈)-cycloalkenylamino, (C₃-C₈)-halocycloalkamino and (C₄-C₈)-halocycloalkenylamino; —C(═W)R¹⁰, OR¹⁰ or NR¹¹ ₂; R⁹ is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyl, where the nine last-mentioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆) alkynyloxy and (C₁-C₆)-haloalkyloxy; R¹⁰ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenyl, where the fourteen last-mentioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkyloxy, (C₂-C₆)-haloalkenyloxy, (C₂-C₆)-haloalkynyloxy, (C₃-C₈)-cycloalkoxy, (C₄-C₈)-cycloalkenyloxy, (C₃-C₈)-halocycloalkoxy, (C₄-C₈)-halocycloalkenyloxy, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkoxy, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkoxy, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenyloxy, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyloxy, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkoxy, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkoxy, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkoxy, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenyloxy, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenyloxy, (C₁-C₄)-alkoxy-(C₁-C₆)-alkoxy, (C₁-C₄)-alkoxy-(C₂-C₆)-alkenyloxy, carbamoyl, (C₁-C₆)-mono- or dialkylcarbamoyl, (C₁-C₆)-mono- or dihaloalkylcarbamoyl, (C₃-C₈)-mono- or dicycloalkylcarbamoyl, (C₁-C₆)-alkoxycarbonyl, (C₃-C₈)-cycloalkoxycarbonyl, (C₁-C₆)-alkanoyloxy, (C₃-C₈)-cycloalkanoyloxy, (C₁-C₆)-haloalkoxycarbonyl, (C₁-C₆)-haloalkanoyloxy, (C₁-C₆)-alkaneamido, (C₁-C₆)-haloalkaneamido, (C₂-C₆)-alkeneamido, (C₃-C₈)-cycloalkaneamido, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkaneamido, (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio, (C₁-C₆)-haloalkylthio, (C₂-C₆)-haloalkenylthio, (C₂-C₆)-haloalkynylthio, (C₃-C₈)-cycloalkylthio, (C₄-C₈)-cycloalkenylthio, (C₃-C₈)-halocycloalkthio, (C₄-C₈)-halocycloalkenylthio, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylthio, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylthio, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylthio, (C₄-C₈)-cycloalkenyl-C₁-C₄)-alkenylthio, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylthio, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylthio, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylthio, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylthio, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylthio, (C₁-C₆)-alkylsulfinyl, (C₂-C₆)-alkenylsulfinyl, (C₂-C₆)-alkynylsulfinyl, (C₁-C₆)-haloalkylsulfinyl, (C₂-C₆)-haloalkenylsulfinyl, (C₂-C₆)-haloalkynylsulfinyl, (C₃-C₈)-cycloalkylsulfinyl, (C₄-C₈)-cycloalkenylsulfinyl, (C₃-C₈)-halocycloalksulfinyl, (C₄-C₈)-halocycloalkenylsulfinyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylsulfinyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylsulfinyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylsulfinyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylsulfinyl₁ (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylsulfinyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylsulfinyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylsulfinyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenyl-sulfinyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₂-C₆)-alkenylsulfonyl, (C₂-C₆)-alkynylsulfonyl, (C₁-C₆)-haloalkylsulfonyl, (C₂-C₆)-haloalkenylsulfonyl, (C₂-C₆)-haloalkynylsulfonyl, (C₃-C₈)-cycloalkylsulfonyl, (C₄-C₈)-cycloalkenylsulfonyl, (C₃-C₈)-halocycloalksulfonyl, (C₄-C₈)-halocycloalkenylsulfonyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylsulfonyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylsulfonyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylsulfonyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylsulfonyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylsulfonyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylsulfonyl, (C₂-C₆)-alkynyl-C₃-C₈)-cycloalkylsulfonyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylsulfonyl, (C₂-C₆)-alkenyl-(C₄-C₈)cycloalkenylsulfonyl, (C₁-C₆)-alkylamino, (C₂-C₆)-alkenylamino, (C₂-C₆)-alkynylamino, (C₁-C₆)-haloalkylamino, (C₂-C₆)-haloalkenylamino, (C₂-C₆)-haloalkynylamino, (C₃-C₈)-cycloalkylamino, (C₄-C₈)-cycloalkenylamino, (C₃-C₈)-halocycloalkamino, (C₄-C₈)-halocycloalkenylamino, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylamino, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylamino, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylamino, (C₄-C₈)cycloalkenyl-(C₁-C₄)-alkenylamino, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylamino, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylamino, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylamino, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylamino, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylamino, (C₁-C₆)-trialkylsilyl, aryl, aryloxy, arylthio, arylamino, aryl-(C₁-C₄)-alkoxy, aryl-(C₂-C₄)-alkenyloxy, aryl-(C₁-C₄)-alkylthio, aryl-(C₂-C₄)-alkenylthio, aryl-(C₁-C₄)-alkylamino, aryl-(C₂-C₄)-alkenylamino, aryl-(C₁-C₆)-dialkylsilyl, diaryl-(C₁-C₆)-alkylsilyl, triarylsilyl and 5- or 6-membered heterocycyl, where the cyclic moiety of the fourteen last-mentioned radicals is optionally substituted by one or more radicals from the group halogen, cyano, nitro, amino, hydroxyl, thio, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₃-C₈)-cycloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-haloalkylthio, (C₁-C₄)-alkylamino, (C₁-C₄)-haloalkylamino, formyl and (C₁-C₄)-alkanoyl; aryl, 5- or 6-membered heteroaromatic, where the two last-mentioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkyloxy, (C₂-C₆)-haloalkenyloxy, (C₂-C₆)-haloalkynyloxy, (C₃-C₈)-cycloalkoxy, (C₄-C₈)-cycloalkenyloxy, (C₃-C₈)-halocycloalkoxy, (C₄-C₈)-halocycloalkenyloxy, carbamoyl, (C₁-C₆)-mono- or dialkylcarbamoyl, (C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-alkanoyloxy, (C₁-C₆)-mono- or dihaloalkylcarbamoyl, (C₁-C₆)-haloalkoxycarbonyl, (C₁-C₆)-haloalkanoyloxy, (C₁-C₆)-alkaneamido, (C₁-C₆)-haloalkaneamido, (C₂-C₆)-alkeneamido, (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio, (C₁-C₆)-haloalkylthio, (C₂-C₆)-haloalkenylthio, (C₂-C₆)-haloalkynylthio, (C₃-C₈)-cycloalkylthio, (C₄-C₈)-cycloalkenylthio, (C₃-C₈)-halocycloalkthio, (C₄-C₈)-halocycloalkenylthio, (C₁-C₆)-alkylsulfinyl, (C₂-C₆)-alkenylsulfinyl, (C₂-C₆)-alkynylsulfinyl, (C₁-C₆)-haloalkylsulfinyl, (C₂-C₆)-haloalkenylsulfinyl, (C₂-C₆)-haloalkynylsulfinyl, (C₃-C₈)-cycloalkylsulfinyl, (C₄-C₈)-cycloalkenylsulfinyl, (C₃-C₈)-halocycloalksulfinyl, (C₄-C₈)-halocycloalkenylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₂-C₆)-alkenylsulfonyl, (C₂-C₆)-alkynylsulfonyl, (C₁-C₆)-haloalkylsulfonyl, (C₂-C₆)-haloalkenylsulfonyl, (C₂-C₆)-haloalkynylsulfonyl, (C₃-C₈)-cycloalkylsulfonyl, (C₄-C₈)-cycloalkenylsulfonyl, (C₃-C₈)-halocycloalkylsulfonyl, (C₄-C₈)-halocycloalkenylsulfonyl, (C₁-C₆)-alkylamino, (C₂-C₆)-alkenylamino, (C₂-C₆)-alkynylamino, (C₁-C₆)-haloalkylamino, (C₂-C₆)-haloalkenylamino, (C₁-C₆)-haloalkynylamino, (C₃-C₈)-cycloalkylamino, (C₄-C₈)-cycloalkenylamino, (C₃-C₈)-halocycloalkamino and (C₄-C₈)-halocycloalkenylamino; R¹¹ is (C₁-C₁₀)-alkyl, haloalkyl, aryl, which is optionally substituted by one or more radicals from the group halogen, cyano, nitro, (C₁-C₄)-alkoxy, (C₁-C₄)-alkyl, amino, (C₁-C₄)-monoalkylamino and (C₁-C₄)-dialkylamino; NR¹⁰ ₂, OR¹⁰ or SR¹⁰ with the proviso that the compounds listed below are not included: 3-(2-chlorophenyl)-1-methyl-5-(4-trifluoromethyl-3-pyridyl)-1H-1,2,4-triazole 3-(2,6-difluorophenyl)-1-methyl-5-(4-trifluoromethyl-3-pyridyl)-1H-1 ,2,4-triazole 3-(2chloro4-fluorophenyl)-1-methyl-5-(4-trifluoromethyl-3-pyridyl)-1H-1,2,4-triazole 3-(3,5-dichlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 5-(4-trifluoromethyl-3-pyridyl)-3-phenyl-1,2,4-oxadiazole 3-(4-trifluoromethyl-3-pyridyl)-5-phenyl-1,2,4-oxadiazole 5-(2-chlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 5-(3-chlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 5-(4-chlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 5-(2-fluorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 5-(4-fluorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 5-(2,4-dichlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 5-(3,4-dichlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 5-(3,5ichlorophenyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-xadiazole 5-(2,6-dichloro4-pynidyl)-3-(4-trifluoromethyl-3-pyridyl)-1,2,4-oxadiazole 5-(3,5-bistrifluoromethylp heny l)-3- (4-trifluoromethyl-3-pyridyl)-1,2,4oxadiazo le 2-(2-chloro phenyl)-5-( 4-trifluoromethyl -3-pyridyl)-1,3,4-xadiazole 2-(3chlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole 2-(4-chlorophenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole 2-(2-trfluoromethoxyphenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazo le 2-(4-trifluoromethoxyphenyl)-5-(4-trifluoromethyl-3-pyridyl)-1,3,4-oxadiazole 2-(4-trifluoromethyl-3-pyridyl)-5-phenyl-1,3,4-oxadiazole 2-(4-trifluoromethyl-3-pyridyl)4-methylthiazolecarbohydrazide ethyl 2-(4-trifluoromethyl-3-pyridyl)-4-methylthiazolecarboxylate N-(4-chlorophenyl)-carbonyl-N′-[2-(4-trifluoromethyl-3-pyridyl)4-methyl-5-thiazolyl]carbonylhydrazine 2-(4-trifluoromethyl-3-pyridyl)4-thiazolecarbohydrazide 4-(4-chlorophenyl)-2-(4-trifluoromethyl-3-pyridyl)thiazole 4-(4-yanophenyl)-2-(4-trifluoromethyl-3-pyridyl)thiazole N-(4-trifluoromethylphenyl)carbonyl—N′-[2-(4-trifluoromethyl-3-pyridyl)4-thiazolyl]carbonylhydrazine 2-(2-(4-trifluoromethyl-3-pyridyl)thiazolyi)-5chloro-3-methylbenzo[b]thiophene 2-(4-chlorophenylmethylthio)-5-(4-trifluoromethyl-3-pyridyl)-1-methyl-1H-1,3,4-triazole 2-(4-chlorophenylcarbonylmethylthio)-5-(4-trifluoromethyl-3-pyridyl)-1-methyl-1H-1,3,4-triazole and 2-ethoxycarbonylmethylthio-5-(4-trifluoromethyl-3-pyridyl)-1-methyl-1H-1,3,4-triazole.
 2. A 4-haloalkyl-3-heterocyclylpyridine or 4-haloalkyl-5-heterocyclylpyrimidine as claimed in claim 1, wherein Y is C₁-C₆-alkyl which is mono- or polysubstituted by chlorine and/or fluorine; m is zero; Q is a 5-membered heterocyclic group

in which a) X²═NR^(a) and X³═CR^(b)R¹⁰ or b) X²═CR^(a)R² and X³═CR^(b)R³or c) X²═CR⁴R⁵ and X³═CR⁶R⁷; R^(a) and R^(b) together are a bond; R^(1,) R², R³, R⁴ and R⁶ are each independently of one another hydrogen, halogen, C₁-C₁₂-alkyl, C₃-C₈-cycloalkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl, where the four last-mentioned hydrocarbon radicals are optionally mono- or polysubstituted by identical or different radicals from a group A1 consisting of C₁-C₆-alkylcarbonyl, C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino, C₁-C₆-alkylcarbonylamino, C₁-C₆-alkylsulfonylamino, phenyl, furyl, pyrryl, thienyl, halogen, cyano, phenyloxy, phenylthio and phenylamino, where the eleven first-mentioned radicals of group A1 are each optionally mono- or polysubstituted by identical or different radicals from a group B1 consisting of halogen, cyano, C₁-C₃-alkoxy and phenyl which is optionally mono- or polysubstituted by one or more halogen atoms and where the three last-mentioned radicals of group A1 are each optionally mono- or polysubstituted by identical or different radicals from a group B2 consisting of halogen, cyano, nitro, C₁-C₃-alkyl and C₁-C₃-alkoxy, or are C₁-C₆-alkylcarbonyl, C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkoxycarbonyl, phenyl, pyridyl, furyl, thienyl, pyrryl, where the eight last-mentioned radicais are optionally mono- or polysubstituted by identical or different radicals from group B1, or are OR^(10, SR) ¹⁰or N(R¹⁰)₂; R⁵ and R⁷ are each independently of one another hydrogen, halogen, C₁-C₁₂-alkyl, C₃-C₈cycloalkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl, where the four last-mentioned hydrocarbon radicals are optionally mono- or polysubstituted by identical or different radicals from a group A2 consisting of C₁-C₆-alkylcarbonyl, C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino, C₁-C₆-alkylcarbonylamino, phenyl, furyl, pyrryl, thienyl, halogen, cyano, phenyloxy, phenylthio and phenylamino, where the ten first-mentioned radicals of group A2 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A2 are each optionally mono- or polysubstituted by identical or different radicals from the group B2, or are C₁-C₆-alkylcarbonyl, C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkoxycarbonyl, phenyl, pyridyl, furyl, thienyl, fluorine, chlorine, bromine, pyrryl, where the eight last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from the group B1, or are OR¹⁰, SR¹⁰ or N(R¹⁰)₂; R¹⁰ is hydrogen, benzyl, C₁-C₆-alkyl, C₁-C₆-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, phenyl, C₁-C₆-alkylcarbonyl or C₁-C₆-alkylsulfonyl, where the eight last-mentioned radicals are optionally mono- or polysubstituted by identical or different halogen atoms.
 3. A 4-haloalkyl-3-heterocyclylpyridine or 4-haloalkyl-5-heterocyclylpyrimidine as claimed in claim 1, wherein Y is trifluoromethyl; R¹, R², R³, R⁴ and R⁶ are each independently of one another halogen, C₁-C₁₂-alkyl, C₂-C₁₂-alkenyl, where the two last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from a group A3 consisting of C₁-C₄-alkylcarbonyl, C₁-C₄-alkylaminocarbonyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylamino, C₁-C₄-alkylcarbonylamino, C₁-C₄-alkylsulfonylamino, phenyl, furyl, pyrryl, thienyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, where the eleven first-mentioned radicals of group A3 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A3 are each optionally mono- or polysubstituted by identical or different radicals from the group B2, or are OR¹⁰, SR¹⁰ or N(R¹⁰)₂; R⁵ and R⁷ are each independently of one another halogen, C₁-C₁₂-alkyl, C₂-C₁₂-alkenyl, where the two last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from a group A4 consisting of C₁-C₄-alkylcarbonyl, C₁-C₄-alkylaminocarbonyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylamino, C₁-C₄-alkylcarbonylamino, phenyl, furyl, pyrryl, thienyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, where the ten first-mentioned radicals of group A4 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A4 are each optionally mono- or polysubstituted by identical or different radicals from the group B2, or are OR¹⁰, SR¹⁰ or N(R¹⁰)₂; R¹⁰ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, phenyl, C₁-C₄-alkylcarbonyl or C₁-C₄-alkylsulfonyl, where the six last-mentioned radicals are optionally mono- or polysubstituted by identical or different halogen atoms.
 4. A 4-haloalkyl-3-heterocyclylpyridine or 4-haloalkyl-5-heterocyclyl-pyrimidine as claimed in claim 1, wherein R¹, R², R³ R⁴ and R⁶ are each independently of one another C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, where the two last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from a group A5 consisting of C₁-C₄-alkylcarbonyl, C₁-C₄-alkylaminocarbonyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylamino, C₁-C₄-alkylcarbonylamino, C₁-C₄-alkylsulfonylamino, phenyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, where the eight first-mentioned radicals of group A5 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A5 are each optionally mono- or polysubstituted by identical or different radicals from the group B2; R⁵ and R⁷ are each independently of one another C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, where the two last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from a group A6 consisting of C₁-C₄-alkylcarbonyl, C₁-C₄-alkylaminocarbonyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylamino, C₁-C₄-alkylcarbonylamino, phenyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, where the seven first-mentioned radicals of group A6 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A6 are each optionally mono- or polysubstituted by identical or different radicals from the group B2.
 5. A process for preparing compounds of the formula I as claimed in claim 1, which comprises reacting, if A) X¹═O, X²═NR^(a), X³═CR^(b)R¹ activated derivatives of the acid of the formula (II),

where X and Y are as defined above, in the presence of a base with a compound of the formula (III),

in which the radical R¹ is as defined in formula (I), or, if B) X¹═S, X²═NR^(a), X³═CR R¹ compounds of the formula (VII) with an electrophilic amination agent

or, if C) X¹═NR^(a), X²═CR^(b)R₁, X³═O amidoximes of the formula (V) with activated derivatives of acids of the formula (VI) or with the acids of the formula (VI) themselves

or, if D) X¹═S, X²═CR^(a)R¹, X³═NR^(b)N,N′-diacylhydrazines of the formula (XIII) with a thiolation agent, such as Lawessons reagent, in an inert solvent

or, if E) X¹═O, X²═CR^(a)R¹, X³═NR^(b) acids of the formula (II) with hydrazides of the formula (X), in which R¹⁰ is as defined above using an activating reagent, such as phosphorus oxychloride or phosphorus pentachloride,

or acid hydrazides of the formula (XI) with orthoesters of the formula (XII), where R¹ is as defined above, and R¹² is (C₁-C₄)-alkyl

or, if F) X¹═O, X²═CR^(a)R², X³═CR^(b)R³ and R^(a), R^(b) and R³ are as defined above, compounds of the formula (XIV) with a dehydrating reagent, such as inorganic acid chlorides, inorganic acids and anhydrides,

or, if G) X¹═S, X²═CR^(a)R², X³═CR^(b)R³ thioamides of the formula (XVII) with carbonyl derivatives of the formula (XVIII) where Z is halogen, in particular chlorine or bromine, acyloxy or sulfonyloxy, in particular methanesulfonyloxy or tolylsulfonyloxy

or, if H) X¹═S, X²═CR⁴R⁵, X³═CR⁶R⁷ thioamides of the formula (XVII) with compounds of the formula (XIX) where the two substituents Z are as defined above and may either be identical or different

or, if I) X¹═NR^(a), X²═CR^(b)R¹, X³═NR⁸ and R^(a), R^(b), R¹ and R⁸ are as defined above, hydrazides of the formula (XX)

with a compound of the formula (XXI) or with thioamides of the formula (XXII),


6. A composition having insecticidal, acaricidal and/or nematicidal action, comprising an effective amount of at least one compound as claimed in claim
 1. 7. The composition according to claim 6, further comprising carriers and/or surfactants.
 8. The composition according to claim 6, further comprising an effective amount of a further active compound selected from the group consisting of acaricides, fungicides, herbicides, insecticides, nematicides and growth-regulating substances.
 9. A veterinary formulation, comprising a compound as claimed in claim 1 or a composition as claimed in claim 6, and a veterinarily acceptable carrier and/or surfactant.
 10. The veterinary formulation according to claim 9, wherein said formulation controls endo- and ectoparasites.
 11. A method for controlling harmful insects, acarina and nematodes, which comprises applying an effective amount of a compound as claimed in claim 1 or of a composition as claimed in claim 6 to the area where the action is desired.
 12. A process for protecting useful plants against the undesired action of harmful insects, acarina and nematodes, which comprises using at least one of the compounds as claimed in claim 1 for treating the seed of the useful plants. 